Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof

ABSTRACT

Provided herein are an organic electronic compound capable of improving luminous efficiency, stability and lifespan of an electronic device, an organic electronic element employing the same, and an electronic device thereof.

BACKGROUND Technical Field

The present invention relates to a compound for an organic electronicelement, an organic electronic element using the same, and an electronicdevice thereof.

Background Art

In general, organic light emitting phenomenon refers to a phenomenonthat converts electric energy into light energy by using an organicmaterial. An organic electronic element using an organic light emittingphenomenon usually has a structure including an anode, a cathode, and anorganic material layer interposed therebetween. Here, in order toincrease the efficiency and stability of the organic electronic element,the organic material layer is often composed of a multi-layeredstructure composed of different materials, and for example, may includea hole injection layer, a hole transport layer, an emitting layer, anelectron transport layer, an electron injection layer and the like.

A material used as an organic material layer in an organic electronicelement may be classified into a light emitting material and a chargetransport material, such as a hole injection material, a hole transportmaterial, an electron transport material, an electron injection materialand the like depending on its function.

Lifespan and efficiency are the most problematic in organicelectroluminescent device, and as displays become larger, these problemsof efficiency and lifespan must be solved. Efficiency, lifespan, anddriving voltage are related to each other, and when the efficiency isincreased, the driving voltage is relatively decreased, and as thedriving voltage is decreased, crystallization of the organic materialdue to Joule heating generated during driving decreases, and as aresult, the lifespan tends to increase.

However, the efficiency cannot be maximized simply by improving theorganic material layer. This is because, when the energy level and T1value between each organic material layer, and the intrinsic propertiesof the material (mobility, interfacial properties, etc.) are optimallycombined, a long lifespan and high efficiency can be achieved at thesame time.

Also, in order to solve the problem of light emission in the holetransport layer in recent organic electroluminescent devices, anemitting-auxiliary layer must exist between the hole transport layer andthe emitting layer, and it is time to develop differentemitting-auxiliary layers according to each emitting layer (R, G, B).

In general, electrons are transferred from the electron transport layerto the emitting layer, and holes are transferred from the hole transportlayer to the emitting layer, and excitons are generated byrecombination.

However, since the material used for the hole transport layer shouldhave a low HOMO value, most have a low T1 value. As a result, excitonsgenerated in the emitting layer are transferred to the hole transportlayer, resulting in charge unbalance in the emitting layer to emit lightat the hole transport layer interface.

When light is emitted at the hole transport layer interface, the colorpurity and efficiency of the organic electronic element are lowered, andthe lifespan is shortened. Therefore, it is urgently required to developan emitting-auxiliary layer having a high T1 value and having a HOMOlevel between the HOMO energy level of the hole transport layer and theHOMO energy level of the emitting layer.

Furthermore, it is necessary to develop a hole injection layer materialthat delays the penetration and diffusion of metal oxides from the anodeelectrode (ITO) into the organic layer, which is one of the causes ofshortening the lifespan of organic electronic element, and that hasstable characteristics, that is, a high glass transition temperature,even against Joule heating generated during device driving. The lowglass transition temperature of the hole transport layer material has acharacteristic of lowering the uniformity of the thin film surfaceduring device driving, which is reported to have a significant effect ondevice lifespan. Moreover, OLED devices are mainly formed by adeposition method, and it is necessary to develop a material that canwithstand a long time during deposition, that is, a material with strongheat resistance.

In other words, in order to fully exhibit the excellent characteristicsof an organic electronic element, the material constituting the organicmaterial layer in the device, such as a hole injection material, a holetransport material, a light emitting material, an electron transportmaterial, an electron injection material, emitting auxiliary layermaterial, etc., is supported by a stable and efficient material. shouldtake precedence, but the development of a stable and efficient organicmaterial layer material for an organic electronic device has not yetbeen sufficiently made. Therefore, the development of new materials iscontinuously required.

DETAILED DESCRIPTION OF THE INVENTION Summary

In order to solve the problems of the above-mentioned background art,the present invention has revealed a compound having a novel structure,and when this compound is applied to an organic electronic element, ithas been found that the luminous efficiency, stability and lifespan ofthe device can be significantly improved.

Accordingly, an object of the present invention is to provide a novelcompound, an organic electronic element using the same, and anelectronic device thereof.

Technical Solution

The present invention provides a compound represented by Formula 1.

In another aspect, the present invention provides an organic electronicelement comprising the compound represented by Formula 1 and anelectronic device thereof.

Effects of the Invention

By using the compound according to the present invention, high luminousefficiency, low driving voltage and high heat resistance of the devicecan be achieved, and color purity and lifespan of the device can begreatly improved.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 to FIG. 3 are each an exemplary view of an organicelectroluminescent device according to the present invention.

FIG. 4 shows a Formula according to an aspect of the present invention.

FIG. 5 shows a driving voltage measurement result for hole mobilityanalysis of an organic electroluminescent device according to an aspectof the present invention.

The numbers in the drawings represent:

100, 200, 300: organic electronic 110: the first electrode element 120:hole injection layer 130: hole transport layer 140: emitting layer 150:electron transport layer 160: electron injection layer 170: secondelectrode 180: light efficiency enhancing Layer 210: buffer layer 220:emitting-auxiliary layer 320: first hole injection layer 330: first holetransport layer 340: first emitting layer 350: first electron transportlayer 360: first charge generation layer 361: second charge generationlayer 420: second hole injection layer 430: second hole transport layer440: second emitting layer 450: second electron transport layer CGL:charge generation layer ST1: first stack ST2: second stack

DETAILED DESCRIPTION

Hereinafter, some embodiments of the present invention will be describedin detail. Further, in the following description of the presentinvention, a detailed description of known functions and configurationsincorporated herein will be omitted when it may make the subject matterof the present invention rather unclear.

In addition, terms, such as first, second, A, B, (a), (b) or the likemay be used herein when describing components of the present invention.Each of these terminologies is not used to define an essence, order orsequence of a corresponding component but used merely to distinguish thecorresponding component from other component(s). It should be noted thatif a component is described as being “connected”, “coupled”, or“connected” to another component, the component may be directlyconnected or connected to the other component, but another component maybe “connected coupled” or “connected” between each component.

As used in the specification and the accompanying claims, unlessotherwise stated, the following is the meaning of the term as follows.

Unless otherwise stated, the term “halo” or “halogen”, as used herein,includes fluorine, bromine, chlorine, or iodine.

Unless otherwise stated, the term “alkyl” or “alkyl group”, as usedherein, has a single bond of 1 to 60 carbon atoms, and means saturatedaliphatic functional radicals including a linear alkyl group, a branchedchain alkyl group, a cycloalkyl group (alicyclic), an cycloalkyl groupsubstituted with a alkyl or an alkyl group substituted with acycloalkyl.

Unless otherwise stated, the term “alkenyl” or “alkynyl”, as usedherein, has double or triple bonds of 2 to 60 carbon atoms, but is notlimited thereto, and includes a linear or a branched chain group.

Unless otherwise stated, the term “cycloalkyl”, as used herein, meansalkyl forming a ring having 3 to 60 carbon atoms, but is not limitedthereto.

Unless otherwise stated, the term “alkoxyl group”, “alkoxy group” or“alkyloxy group”, as used herein, means an oxygen radical attached to analkyl group, but is not limited thereto, and has 1 to 60 carbon atoms.

Unless otherwise stated, the term “aryloxyl group” or “aryloxy group”,as used herein, means an oxygen radical attached to an aryl group, butis not limited thereto, and has 6 to 60 carbon atoms.

The terms “aryl group” and “arylene group” used in the present inventionhave 6 to 60 carbon atoms, respectively, unless otherwise specified, butare not limited thereto. In the present invention, an aryl group or anarylene group means a single ring or multiple ring aromatic, andincludes an aromatic ring formed by an adjacent substituent joining orparticipating in a reaction.

For example, the aryl group may be a phenyl group, a biphenyl group, afluorene group, or a spirofluorene group.

The prefix “aryl” or “ar” means a radical substituted with an arylgroup. For example, an arylalkyl may be an alkyl substituted with anaryl, and an arylalkenyl may be an alkenyl substituted with aryl, and aradical substituted with an aryl has a number of carbon atoms as definedherein.

Also, when prefixes are named subsequently, it means that substituentsare listed in the order described first. For example, an arylalkoxymeans an alkoxy substituted with an aryl, an alkoxylcarbonyl means acarbonyl substituted with an alkoxyl, and an arylcarbonylalkenyl alsomeans an alkenyl substituted with an arylcarbonyl, wherein thearylcarbonyl may be a carbonyl substituted with an aryl.

Unless otherwise stated, the term “heterocyclic group”, as used herein,contains one or more heteroatoms, but is not limited thereto, has 2 to60 carbon atoms, includes any one of a single ring or multiple ring, andmay include heteroaliphadic ring and heteroaromatic ring. Also, theheterocyclic group may also be formed in conjunction with an adjacentgroup.

Unless otherwise stated, the term “heteroatom”, as used herein,represents at least one of N, O, S, P, or Si.

Also, the term “heterocyclic group” may include a ring including SO₂instead of carbon consisting of cycle. For example, “heterocyclic group”includes the following compound.

Unless otherwise stated, the term “fluorenyl group” or “fluorenylenegroup”, as used herein, means a monovalent or divalent functional group,in which R, R′ and R″ are all hydrogen in the following structures, andthe term “substituted fluorenyl group” or “substituted fluorenylenegroup” means that at least one of the substituents R, R′, R″ is asubstituent other than hydrogen, and include those in which R and R′ arebonded to each other to form a spiro compound together with the carbonto which they are bonded.

The term “spiro compound”, as used herein, has a ‘spiro union’, and aspiro union means a connection in which two rings share only one atom.At this time, atoms shared in the two rings are called ‘spiro atoms’,and these compounds are called ‘monospiro-’, ‘di-spiro-’ and‘tri-spiro-’, respectively, depending on the number of spiro atoms in acompound.

Unless otherwise stated, the term “aliphatic”, as used herein, means analiphatic hydrocarbon having 1 to 60 carbon atoms, and the term“aliphatic ring”, as used herein, means an aliphatic hydrocarbon ringhaving 3 to 60 carbon atoms.

Unless otherwise stated, the term “ring”, as used herein, means analiphatic ring having 3 to 60 carbon atoms, or an aromatic ring having 6to 60 carbon atoms, or a hetero ring having 2 to 60 carbon atoms, or afused ring formed by the combination of them, and includes a saturatedor unsaturated ring.

Other hetero compounds or hetero radicals other than the above-mentionedhetero compounds include, but are not limited thereto, one or moreheteroatoms.

Also, unless expressly stated, as used herein, “substituted” in the term“substituted or unsubstituted” means substituted with one or moresubstituents selected from the group consisting of deuterium, halogen,an amino group, a nitrile group, a nitro group, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxyl group, a C₁-C₂₀ alkylamine group, a C₁-C₂₀ alkylthiopengroup, a C₆-C₂₀ arylthiopen group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀alkynyl group, a C₃-C₂₀ cycloalkyl group, a C₆-C₂₀ aryl group, a C₆-C₂₀aryl group substituted by deuterium, a C₈-C₂₀ arylalkenyl group, asilane group, a boron group, a germanium group, and a C₂-C₂₀heterocyclic group, but is not limited to these substituents.

Also, unless there is an explicit explanation, the formula used in thepresent invention is the same as the definition of the substituent bythe exponent definition of the following formula.

Here, when a is an integer of zero, the substituent R¹ is absent, when ais an integer of 1, the sole substituent R¹ is linked to any one of thecarbon constituting the benzene ring, when a is an integer of 2 or 3,each is combined as follows, where R¹ may be the same or different fromeach other, when a is an integer of 4 to 6, it is bonded to the carbonof the benzene ring in a similar manner, while the indication of thehydrogen bonded to the carbon forming the benzene ring is omitted.

Hereinafter, a compound according to an aspect of the present inventionand an organic electronic element including the same will be described.

The present invention provides a compound represented by Formula 1.

wherein, each symbol may be defined as follows.

1) R¹, R², R³ and R⁴ are the same or different from each other, and areeach independently selected from the group consisting of a hydrogen;deuterium; halogen; a C₆-C₆₀ aryl group; fluorenyl group; a C₂-C₆₀heterocyclic group including at least one heteroatom of O, N, S, Si orP; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromaticring; C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynylgroup; a C₁-C₃₀ alkoxy group; a C₆-C₃₀ aryloxy group; or an adjacentplurality of R¹s, or a plurality of R²s, or a plurality of R³s, or aplurality of R⁴s may be bonded to each other to form a ring.

When R¹, R², R³ and R⁴ are an aryl group, it may be preferably a C₆-C₃₀aryl group, and more preferably a C₆-C₂₅ aryl group, for example, it maybe phenyl, biphenyl, naphthyl, terphenyl, etc.

When R¹, R², R³ and R⁴ are a heterocyclic group, it may be preferably aC₂-C₃₀ heterocyclic group, and more preferably a C₂-C₂₄ heterocyclicgroup, for example, it may be pyrazine, thiophene, pyridine,pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline,benzoquinazoline, carbazole, dibenzoquinazole, dibenzofuran,dibenzothiophene, benzothienopyrimidine, benzofuropyrimidine,phenothiazine, phenylphenothiazine, etc.

When R¹, R², R³ and R⁴ are a fused ring group, it may be preferably afused ring group of a C₃-C₃₀ aliphatic ring and a C₆-C₃₀ aromatic ring,more preferably a fused ring group of a C₃-C₂₄ aliphatic ring and aC₆-C₂₄ aromatic ring.

When R¹, R², R³ and R⁴ are an alkyl group, it may be preferably a C₁-C₃₀alkyl group, and more preferably a C₁-C₂₄ alkyl group.

When R¹, R², R³ and R⁴ are an alkoxy group, it may be preferably aC₁-C₂₄ alkoxy group.

When R¹, R², R³ and R⁴ are an aryloxy group, it may be preferably aC₁-C₂₄ aryloxy group.

2) X and Y are independently of each other are O or S,

3) L¹, L² and L³ are each independently selected from the groupconsisting of single bond; a C₆-C₆₀ arylene group; a fluorenylene group;a C₂-C₆₀ heterocyclic group including at least one heteroatom of O, N,S, Si or P; and a fused ring group of a C₃-C₆₀ aliphatic ring and aC₆-C₆₀ aromatic ring;

4) L⁴ is selected from the group consisting of a C₆-C₆₀ arylene group; afluorenylene group; a C₂-C₆₀ heterocyclic group including at least oneheteroatom of O, N, S, Si or P; and a fused ring group of a C₃-C₆₀aliphatic ring and a C₆-C₆₀ aromatic ring;

Wherein L¹, L², L³ and L⁴ are an arylene group, it may be preferably aC₆-C₃₀ arylene group, more preferably a C₆-C₂₄ arylene group, forexample, phenylene, biphenyl, naphthalene, terphenyl, etc.

Wherein L¹, L², L³ and L⁴ are a heterocyclic group, it may be preferablya C₂˜C₃₀ heterocyclic group, and more preferably a C₂˜C₂₄ heterocyclicgroup, for example, pyrazine, thiophene, pyridine, pyrimidoindole,5-phenyl-5H-pyrimido[5,4-b]indole, quinazoline, benzoquinazoline,carbazole, dibenzoquinazole, dibenzofuran, dibenzothiophene,benzothienopyrimidine, benzofuropyrimidine, phenothiazine,phenylphenothiazine, etc.

Wherein L¹, L², L³ and L⁴ are fused ring groups, it may be preferably afused ring group of a C₃-C₃₀ aliphatic ring and a C₆-C₃₀ aromatic ring,more preferably a fused ring group of a C₃-C₂₄ aliphatic ring and aC₆-C₂₄ aromatic ring.

5) Ar¹, Ar², Ar³, Ar⁴ and Ar⁵ are each independently selected from thegroup consisting of a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀heterocyclic group including at least one heteroatom of O, N, S, Si orP; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromaticring; a C₁-C₆₀ alkyl group; an C₂˜C₃₀ alkenyl group; a C₂-C₂₀ alkynylgroup; a C₁-C₃₀ alkoxy group; a C₆-C₃₀ aryloxy group;

Wherein Ar¹, Ar², Ar³, Ar⁴ and Ar⁵ are an aryl group, they may bepreferably a C₆-C₃₀ aryl group, most preferably a C₆-C₂₅ aryl group,exemplarily, they may be phenyl, biphenyl, naphthyl, terphenyl, and thelike.

Wherein Ar¹, Ar², Ar³, Ar⁴ and Ar⁵ are a heterocyclic group, they may bepreferably a C₂-C₃₀ heterocyclic group, and more preferably a C₂-C₂₄heterocyclic group, for example, they may be pyrazine, thiophene,pyridine, pyrimidoindole, 5-phenyl-5H-pyrimido[5,4-b]indole,quinazoline, benzoquinazoline, carbazole, dibenzoquinazole,dibenzofuran, dibenzothiophene, benzothienopyrimidine,benzofuropyrimidine, phenothiazine, phenylphenothiazine, etc.

Wherein Ar¹, Ar², Ar³, Ar⁴ and Ar⁵ are a fused ring group, they may bepreferably a fused ring group of a C₃-C₃₀ aliphatic ring and a C₆-C₃₀aromatic ring, more preferably a fused ring group of a C₃-C₂₄ aliphaticring and a C₆-C₂₄ aromatic ring.

Wherein Ar¹, Ar², Ar³, Ar⁴ and Ar⁵ are an alkyl group, they may bepreferably an C₁˜C₃₀ alkyl group, more preferably an C₁˜C₂₄ alkyl group.

Wherein Ar¹, Ar², Ar³, Ar⁴ and Ar⁵ are an alkoxy group, they may bepreferably a C₁-C₂₄ alkoxy group.

Wherein Ar¹, Ar², Ar³, Ar⁴ and Ar⁵ are an aryloxy group, they may bepreferably a C₁-C₂₄ aryloxy group.

6) a and d are each independently an integer of 0 to 4, b and c are eachindependently an integer of 0 to 3, m and n are each independently 0 or1, provided that m+n≥1; 7) provided that the compound of Formula 1excludes is a compound represented by Formula 7:

8) wherein R¹, R², R³, R⁴, X, Y, L¹, L², L⁴, Ar¹, Ar², Ar³, a, b and care the same as defined in Formula 1, d′ is an integer from 0 to 3,

9) wherein the aryl group, arylene group, heterocyclic group, fluorenylgroup, fluorenylene group, aliphatic ring group, fused ring group, alkylgroup, alkenyl group, alkoxyl group and aryloxy group may be substitutedwith one or more substituents selected from the group consisting ofdeuterium; halogen; silane group; siloxane group; boron group; germaniumgroup; cyano group; nitro group; C₁-C₂₀ alkylthio group; C₁-C₂₀ alkoxygroup; C₁-C₂₀ alkyl group; C₂-C₂₀ alkenyl group; C₂-C₂₀ alkynyl group;C₆-C₂₀ aryl group; C₆-C₂₀ aryl group substituted with deuterium; afluorenyl group; C₂˜C₂₀ heterocyclic group; C₃-C₂₀ cycloalkyl group;C₇-C₂₀ arylalkyl group; and C₈-C₂₀ arylalkenyl group; also thesubstituents may be bonded to each other to form a saturated orunsaturated ring, wherein the term ‘ring’ means a C₃-C₂₀ aliphatic ringor a C₆-C₆₀ aromatic ring or a C₂-C₆₀ heterocyclic group or a fused ringformed by the combination thereof.

Also, the present invention provides a compound wherein L¹, L², L³ andL⁴ are represented by any one of Formulas b-1 to b-13.

{wherein

1) Z is O, S, C(R¹³)(R¹⁴) or N-L⁵-Ar⁶,

2) Z¹, Z², Z³, Z⁴ and Z⁵ are each independently N or C(R¹⁵), providedthat at least one of Z¹, Z², Z³, Z⁴ and Z⁵ is C(R¹⁵), at least one is N;

3) R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴ and R¹⁵ are the same asthe definition of R¹ in Formula 1, or adjacent groups may combine witheach other to form a ring,

4) e, g, h and l are each independently an integer of 0 to 4, f is aninteger of 0 to 6, i and j are each independently an integer of 0 to 3,k is an integer of 0 to 2,

5) Ar⁶ is the same as the definition of Ar¹ in Formula 1,

6) L⁵ is the same as the definition of L¹ in Formula 1,

7)

indicates the binding position.}

Also, the compound represented by Formula 1 is represented by any one ofFormulas 1-1 to 1-3

{wherein

1) R¹, R², R³, R⁴, X, Y, L¹, L², L³, L⁴, Ar¹, Ar², Ar³, Ar⁴, Ar⁵, a, b,c and d are the same as defined in Formula 1,

2) c′ is an integer from 0 to 2, and d′ is an integer from 0 to 3.}

Also, the compound represented by Formula 1 is represented by any one ofFormulas 2-1 to 2-4.

{wherein

R¹, R², R³, R⁴, X, Y, L¹, L², L³, L⁴, Ar¹, Ar², Ar³, Ar⁴, Ar⁵, a, b, c,d, m and n are the same as defined in Formula 1}

Also, the compound represented by Formula 1 is represented by any one ofFormulas 3-1 to 3-14

{wherein

1) R¹, R², R³, R⁴, X, Y, L¹, L², L³, L⁴, Ar¹, Ar², Ar³, Ar⁴, Ar⁵, a, b,c and d are the same as defined in Formula 1,

2) c′ is an integer from 0 to 2, and d′ is an integer from 0 to 3}

Also, the compound represented by Formula 1 is represented by any one ofFormulas 4-1 to 4-6.

{wherein

1) R¹, R², R³, R⁴, X, Y, L¹, L², L³, Ar¹, Ar², Ar³, Ar⁴, Ar⁵, a, b, c,d, m and n are the same as defined in Formula 1,

2) R⁵, R⁶, R⁷, R⁹, R¹⁰, R¹¹, R¹², e, f, g, i, j, k, l and Z are the sameas defined in Formulas b-1 to b-13.}

Also, the compound represented by Formula 1 is represented by any one ofFormulas 5-1 to 5-4

{wherein

R¹, R², R³, R⁴, X, Y, L¹, L², L³, L⁴, Ar¹, Ar², Ar³, Ar⁴, Ar⁵, a, b, c,d, m and n are the same as defined in Formula 1.}

Also, the compound represented by Formula 1 is represented by any one ofFormulas 6-1 to 6-40

{wherein

1) R¹, R², R³, R⁴, X, Y, L¹, L², L³, L⁴, Ar¹, Ar², Ar³, Ar⁴, Ar⁵, a, b,c and d are the same as defined in Formula 1.}

2) c′ is an integer from 0 to 2, and d′ is an integer from 0 to 3.}

Also, the compound represented by Formula 1 is represented by any one ofthe following compounds P-1 to P-152.

Referring to FIG. 1, the organic electronic element (100) according tothe present invention includes a first electrode (110), a secondelectrode (170), and an organic material layer including a singlecompound or 2 or more compounds represented by Formula 1 between thefirst electrode (110) and the second electrode (170). In this case, thefirst electrode (110) may be an anode, and the second electrode (170)may be a cathode. In the case of an inverted type, the first electrodemay be a cathode and the second electrode may be an anode.

The organic material layer may sequentially include a hole injectionlayer (120), a hole transport layer (130), an emitting layer (140), anelectron transport layer (150), and an electron injection layer (160) onthe first electrode (110). In this case, the remaining layers except forthe emitting layer (140) may not be formed. It may further include ahole blocking layer, an electron blocking layer, an emitting-auxiliarylayer (220), a buffer layer (210), etc. and the electron transport layer(150) and the like may serve as a hole blocking layer. (See FIG. 2)

Also, the organic electronic element according to an embodiment of thepresent invention may further include a protective layer or a lightefficiency enhancing layer (180). The light efficiency enhancing layermay be formed on one of both surfaces of the first electrode not incontact with the organic material layer or on one of both surfaces ofthe second electrode not in contact with the organic material layer. Thecompound according to an embodiment of the present invention applied tothe organic material layer may be used as a host or dopant of the holeinjection layer (120), the hole transport layer (130), theemitting-auxiliary layer (220), electron transport auxiliary layer, theelectron transport layer (150), and an electron injection layer (160),the emitting layer (140) or as a material for the light efficiencyenhancing layer. Preferably, for example, the compound according toFormula 1 of the present invention may be used as a material of theemitting-auxiliary layer or the emitting layer.

The organic material layer may include 2 or more stacks including a holetransport layer, an emitting layer and an electron transport layersequentially formed on the anode, further include a charge generationlayer formed between the 2 or more stacks (see FIG. 3).

Otherwise, even with the same core, the band gap, electricalcharacteristics, interface characteristics, etc. may vary depending onwhich position the substituent is bonded to, therefore the choice ofcore and the combination of sub-substituents bound thereto are also veryimportant, and in particular, when the optimal combination of energylevels and T1 values and unique properties of materials (mobility,interfacial characteristics, etc.) of each organic material layer isachieved, a long lifespan and high efficiency can be achieved at thesame time.

The organic electroluminescent device according to an embodiment of thepresent invention may be manufactured using a PVD (physical vapordeposition) method. For example, depositing a metal or a metal oxidehaving conductivity or an alloy thereof on a substrate to form an anode,and after forming an organic material layer including the hole injectionlayer (120), the hole transport layer (130), the emitting layer (140),the electron transport layer (150) and the electron injection layer(160) thereon, it can be prepared by depositing a material that can beused as a cathode thereon.

Also, in the present invention, the organic material layer is formed byany one of a spin coating process, a nozzle printing process, an inkjetprinting process, a slot coating process, a dip coating process, and aroll-to-roll process, and the organic material layer provides an organicelectronic element comprising the compound as an electron transportmaterial.

As another specific example, the same or different compounds of thecompound represented by Formula 1 are mixed and used in the organicmaterial layer.

Also, the present invention provides an emitting-auxiliary layercomposition comprising the compound represented by Formula 1, andprovides an organic electronic element including the emitting-auxiliarylayer.

Also, the present invention provides a hole transport layer compositioncomprising the compound represented by Formula 1, and provides anorganic electronic element including the hole transport layer.

Also, the present invention provides a light efficiency enhancing layercomposition comprising the compound represented by Formula 1, andprovides an organic electric device including the light efficiencyenhancing layer.

Also, the present invention provides an electronic device comprising adisplay device including the organic electronic element; and a controlunit for driving the display device;

In another aspect, the organic electronic element is at least one of anorganic electroluminescent device, an organic solar cell, an organicphotoreceptor, an organic transistor, and a device for monochromatic orwhite lighting. At this time, the electronic device may be a current orfuture wired/wireless communication terminal, and covers all kinds ofelectronic devices including mobile communication terminals such asmobile phones, a personal digital assistant (PDA), an electronicdictionary, a point-to-multipoint (PMP), a remote controller, anavigation unit, a game player, various kinds of TVs, and various kindsof computers.

Hereinafter, a synthesis example of the compound represented by Formula1 of the present invention and a manufacturing example of an organicelectronic element of the present invention will be described in detailwith reference to Examples, but the present invention is not limited tothe following Examples.

Synthesis Example 1

The compound represented by Formula 1 according to the present invention(Final product) may be prepared by reacting as shown in Scheme 1 below,but is not limited thereto. Hal¹ to Hal³ are I, Br or Cl.

I. Synthesis of Sub-1

Sub-1 of Scheme 1 is synthesized by the reaction routes of Schemes 2 and3 below, but is not limited thereto. Hal¹ to Hal⁵ are 1, Br or Cl.

1. Synthesis of Sub-1-1

(1) Synthesis of Sub-1-g-1

After dissolving Sub-1-e-1 (30.0 g, 60.5 mmol) in THE (302 mL) in around-bottom flask, Sub-1-f-1 (12.1 g, 60.5 mmol), Pd(PPh₃)₄ (4.2 g, 3.6mmol), NaOH (7.3 g, 181.4 mmol), H₂O (151 mL) were added and stirred at80° C. After the reaction was completed, the mixture was extracted withCH₂Cl₂ and water, the organic layer was dried over MgSO₄, concentrated,and the resulting compound was recrystallized by silicagel column toobtain 15.0 g of a product. (Yield: 69%)

(2) Synthesis of Sub-1-1

The obtained Sub-1-g-1 (15.0 g, 41.7 mmol) was placed in a round-bottomflask with Pd(OAc)₂ (0.5 g, 2.1 mmol) and 3-nitropyridine (0.3 g, 2.1mmol), after dissolving in C₆F₆ (62 mL) and DMI (42 mL),tert-butylperoxybenzoate (16.2 g, 83.4 mmol) was added and the mixturewas stirred at 90° C. After the reaction was completed, the mixture wasextracted with CH₂Cl₂ and water, the organic layer was dried over MgSO₄,concentrated, and the resulting compound was recrystallized by silicagelcolumn to obtain 9.4 g of a product. (Yield: 63%)

2. Synthesis of Sub-1-2

(1) Synthesis of Sub-1-g-2

After placing Sub-1-e-2 (30.0 g, 105.8 mmol), THE (529 mL), Sub-1-f-2(26.5 g, 105.8 mmol), Pd(PPh₃)₄ (7.3 g, 6.4 mmol), NaOH (12.7 g, 317.4mmol), H₂O (265 mL) in a round-bottom flask, 29.0 g of the product wasobtained in the same manner as in Sub-1-g-1 at 80° C. (Yield: 67%)

(2) Synthesis of Sub-1-2

The obtained Sub-1-g-2 (29.0 g, 70.9 mmol) was dissolved in a roundbottom flask, after Pd(OAc)₂ (0.8 g, 3.5 mmol), 3-nitropyridine (0.4 g,3.5 mmol), C₆F₆ (106 mL), DMI (71 mL), tert-butyl peroxybenzoate (27.5g, 141.8 mmol) were added, 17.9 g of the product was obtained byperforming an experiment at 90° C. in the same manner as in Sub-1-1.(Yield: 62%)

3. Synthesis of Sub-1-55

(1) Synthesis of Sub-1-c-55

After dissolving Sub-1-a-55 (30.0 g, 106.0 mmol) in THE (530 mL) in around-bottom flask, Sub-1-b-55 (29.5 g, 106.0 mmol), Pd(PPh₃)₄ (7.4 g,6.4 mmol), NaOH (12.7 g, 318.1 mmol), H₂O (265 mL) were added andstirred at 80° C. After the reaction was completed, the mixture wasextracted with CH₂Cl₂ and water, the organic layer was dried over MgSO₄,concentrated, and the resulting compound was recrystallized by silicagelcolumn to obtain 33.1 g of a product. (Yield: 80%)

(2) Synthesis of Sub-1-d-55

Sub-1-c-55 (33.1 g, 84.8 mmol), H₂O₂ (8.5 mL), and acetic acid (339 mL)were placed in a round bottom flask and stirred at room temperature.When the reaction was completed, acetic acid was removed and water wasadded to obtain a solid, and the solid was dissolved in CH₂Cl₂ andconcentrated on silicagel column to obtain 30.6 g of the product.(Yield: 89%)

(3) Synthesis of Sub-1-55

Sub-1-d-55 (30.6 g, 405.73 mmol) was dissolved in an excess of H₂SO₄(91.9 mL) in a round bottom flask, followed by stirring at roomtemperature for 6 hours. When the reaction was completed, the reactionwas neutralized using an aqueous NaOH solution, extracted with CH₂Cl₂,the organic layer was dried over MgSO₄, concentrated, and the resultingcompound was recrystallized by silicagel column to obtain 24.3 g of aproduct. (Yield: 86%)

4. Synthesis of Sub-1-83

(1) Synthesis Sub-1-c-83

After placing Sub-1-a-83 (30.0 g, 147.1 mmol), THE (735 mL), Sub-1-b-83(41.4 g, 147.1 mmol), Pd(PPh₃)₄ (10.2 g, 8.8 mmol), NaOH (17.7 g, 441.2mmol), H₂O (368 mL) in a round-bottom flask, the experiment wasperformed in the same manner as in Sub-1-g-1 at 80° C. to obtain 33.2 gof the product. (Yield: 72%)

(2) Synthesis Sub-1-d-83

Sub-1-c-83 (33.2 g, 105.9 mmol), H₂O₂ (10.6 mL), acetic acid (424 mL)were placed in a round-bottom flask and tested in the same manner as inSub-1-d-55 at room temperature to obtain 31.4 g of the product. (Yield:90%)

(3) Synthesis Sub-1-83

Sub-1-d-83 (31.4 g, 95.3 mmol) and H₂SO₄ (94.2 mL) were added anddissolved, followed by the same experiment as in Sub-1-55 to obtain 25.0g of the product. (Yield: 88%)

5. Synthesis of Sub-1-97

(1) Synthesis of Sub-1-g-97

After placing Sub-1-e-97 (30.0 g, 100.4 mmol), THE (502 mL), Sub-1-f-97(36.0 g, 100.4 mmol), Pd(PPh₃)₄ (7.0 g, 6.0 mmol), NaOH (12.0 g, 301.1mmol), H₂O (251 mL) in a round flask, the experiment was performed inthe same manner as in Sub-1-g-1 above at 80° C. to obtain 34.1 g of theproduct. (Yield: 70%)

(2) Synthesis of Sub-1-97

After dissolving Sub-1-g-97 (34.1 g, 70.3 mmol) in a round-bottomedflask, Pd(OAc)₂ (0.8 g, 3.5 mmol), 3-nitropyridine (0.4 g, 3.5 mmol),C₆F₆ (105 mL), DMI (70 mL), tert-butylperoxybenzoate (27.3 g, 140.5mmol) were added, and the experiment was performed in the same manner asin Sub-1-1 above at 90° C. 21.1 g of the product was obtained. (Yield:63%)

6. Synthesis of Sub-1-114

(1) Synthesis of Sub-1-c-114

After placing Sub-1-a-114 (30.0 g, 149 mmol), THE (750 mL), Sub-1-b-114(42.5 g, 149 mmol), Pd(PPh₃)₄ (10.4 g, 8.96 mmol), NaOH (17.9 g, 448mmol) and H₂O (375 mL) in a round-bottom flask, the experiment wasperformed in the same manner as in Sub-1-g-1 at 80° C. to obtain 39.4 gof the product. (Yield: 84%)

(2) Synthesis of Sub-1-d-114

Sub-1-c-114 (39.4 g, 126 mmol), H₂O₂ (35.9 mL), and acetic acid (500 mL)were placed in a round-bottom flask, and at room temperature, 38.1 g ofthe product was obtained by performing an experiment in the same manneras for Sub-1-d-55. (Yield: 92%)

(3) Synthesis of Sub-1-d-114

Sub-1-d-114 (38.1 g, 115 mmol) and H₂SO₄ (114 mL) were added anddissolved, followed by the same procedure as in Sub-1-55 to obtain 30.2g of the product. (Yield: 88%)

7. Synthesis Example of Sub-1-127

(1) Synthesis of Sub-1-g-127

After placing Sub-1-e-127 (30.0 g, 127 mmol), THE (640 mL), Sub-1-f-127(31.6 g, 127 mmol), Pd(PPh₃)₄ (8.82 g, 7.63 mmol), NaOH (15.3 g, 382mmol), H₂O (320 mL) in a round-bottom flask, the experiment wasperformed in the same manner as in Sub-1-g-1 at 80° C. to obtain 35.7 gof the product. (Yield: 78%)

(2) Synthesis of Sub-1-127

After dissolving Sub-1-g-127 (35.7 g, 99.2 mmol) in a round-bottomflask, Pd(OAc)₂ (1.11 g, 4.96 mmol), 3-nitropyridine (0.62 g, 4.96mmol), C₆F₆ (148 mL), DMI (99 mL), tert-butylperoxybenzoate (38.5 g, 198mmol) were added and tested in the same manner as in Sub-1-1 at 90° C.to obtain 14.9 g of the product. (Yield: 42%)

8. Synthesis Example of Sub-1-131

(1) Synthesis of Sub-1-c-131

After putting Sub-1-a-131 (30.0 g, 157 mmol), THE (780 mL), Sub-1-b-131(38.7 g, 157 mmol), Pd(PPh₃)₄ (10.9 g, 9.40 mmol), NaOH (18.8 g, 470mmol), H₂O (390 mL) in a round-bottom flask, the experiment wasperformed at 80° C. in the same manner as in Sub-1-g-1 to obtain 40.3 gof the product. (Yield: 82%)

(2) Synthesis of Sub-1-d-131

Sub-1-c-131 (40.3 g, 129 mmol), H₂O₂ (36.7 mL) and acetic acid (515 mL)were placed in a round-bottom flask and tested in the same manner as inSub-1-d-55 at room temperature to produce the product 38.5 g wereobtained. (Yield: 91%)

(3) Synthesis of Sub-1-131

Sub-1-d-131 (38.5 g, 117 mmol) and H₂SO₄ (116 mL) were added anddissolved, followed by the same experiment as in Sub-1-55 to obtain 32.4g of the product. (Yield: 93%)

9. Synthesis of Sub-1-132

(1) Synthesis of Sub-1-g-132

After placing Sub-1-f-132 (30.0 g, 72.2 mmol), THE (360 mL), Sub-1-e-132(10.0 g, 72.2 mmol), Pd(PPh₃)₄ (5.0 g, 4.33 mmol), NaOH (8.7 g, 217mmol), H₂O (180 mL) in a round-bottom flask, 18.7 g of the product wereobtained by performing an experiment in the same manner as in Sub-1-g-1at 80° C. (Yield: 72%)

(2) Synthesis of Sub-1-132

After dissolving Sub-1-g-132 (18.7 g, 52.0 mmol) in a round-bottomflask, Pd(OAc)₂ (0.58 g, 2.60 mmol), 3-nitropyridine (0.32 g, 2.60mmol), C₆F₆ (78 mL), DMI (52 mL), tert-butylperoxybenzoate (20.2 g, 104mmol) were added and tested in the same manner as in Sub-1-1 at 90° C.to obtain 12.6 g of the product. (Yield: 68%)

10. Synthesis Example of Sub-1-133

(1) Synthesis of Sub-1-c-133

After placing Sub-1-a-133 (30.0 g, 192 mmol), THE (960 mL), Sub-1-b-133(63.1 g, 192 mmol), Pd(PPh₃)₄ (13.3 g, 11.5 mmol), NaOH (23.0 g, 576mmol), H₂O (480 mL) in a round-bottom flask, 48.1 g of the product wasobtained by performing an experiment in the same manner as in Sub-1-g-1at 80° C. (Yield: 80%)

(2) Synthesis of Sub-1-d-133

Sub-1-c-133 (48.1 g, 154 mmol), H₂O₂ (43.9 mL), and acetic acid (614 mL)were placed in a round-bottom flask, at room temperature, 44.5 g of theproduct was obtained in the same manner as in Sub-1-d-55. (Yield: 88%)

(3) Synthesis of Sub-1-133

Sub-1-d-133 (44.5 g, 135 mmol) and H₂SO₄ (134 mL) were added anddissolved, followed by the same experiment as in Sub-1-55 to obtain 36.6g of the product. (Yield: 91%)

The compound belonging to Sub-1 may be the following compounds, but isnot limited thereto, and Table 1 below shows Field Desorption-MassSpectrometry (FD-MS) values of the compounds belonging to Sub-1.

TABLE 1 compound FD-MS compound FD-MS Sub-1-1 m/z = 355.96(C₁₈H₁₀BrClO =357.63) Sub-1-2 m/z = 405.98(C₂₂H₁₂BrClO = 407.69) Sub-1-3 m/z =355.96(C₁₈H₁₀BrClO = 357.63) Sub-1-4 m/z = 355.96(C₁₈H₁₀BrClO = 357.63)Sub-1-5 m/z = 447.97(C₂₄H₁₄BrClS = 449.79) Sub-1-6 m/z =447.97(C₂₄H₁₄BrClS = 449.79) Sub-1-7 m/z = 447.97(C₂₄H₁₄BrClS = 449.79)Sub-1-8 m/z = 524.00(C₃₀H₁₈BrClS = 525.89) Sub-1-6 m/z =445.97(C₂₄H₁₂BrClO₂ = 447.71) Sub-1-10 m/z = 596.05(C₃₇H₂₂BrClO =597.94) Sub-1-11 m/z = 461.95(C₂₄H₁₂BrClOS = 463.77) Sub-1-12 m/z =521.02(C₃₀H₁₇BrClNO = 522.83) Sub-1-13 m/z = 477.93(C₂₄H₁₂BrClS₂ =479.83) Sub-1-14 m/z = 526.99(C₂₇H₁₅BrClN₃S = 528.85) Sub-1-15 m/z =610.02(C₃₇H₂₀BrClS = 611.98) Sub-1-16 m/z = 471.97(C₂₆H₁₄BrClS = 473.81)Sub-1-17 m/z = 355.96(C₁₈H₁₀BrClO = 357.63) Sub-1-18 m/z =355.96(C₁₈H₁₀BrClO = 357.63) Sub-1-19 m/z = 355.96(C₁₈H₁₀BrClO = 357.63)Sub-1-20 m/z = 421.95(C₂₂H₁₂BrClS = 423.75) Sub-1-21 m/z =405.98(C₂₂H₁₂BrClO = 407.69) Sub-1-22 m/z = 431.99(C₂₄H₁₄BrClO = 433.73)Sub-1-23 m/z = 447.97(C₂₄H₁₄BrClS = 449.79) Sub-1-24 m/z =431.99(C₂₄H₁₄BrClO = 433.73) Sub-1-25 m/z = 447.97(C₂₄H₁₄BrClS = 449.79)Sub-1-26 m/z = 447.97(C₂₄H₁₄BrClS = 449.79) Sub-1-27 m/z =431.99(C₂₄H₁₄BrClO = 433.73) Sub-1-28 m/z = 447.97(C₂₄H₁₄BrClS = 449.79)Sub-1-29 m/z = 447.97(C₂₄H₁₄BrClS = 449.79) Sub-1-30 m/z =447.97(C₂₄H₁₄BrClS = 449.79) Sub-1-31 m/z = 508.02(C₃₀H₁₈BrClO = 509.83)Sub-1-32 m/z = 508.02(C₃₀H₁₈BrClO = 509.83) Sub-1-33 m/z =508.02(C₃₀H₁₈BrClO = 509.83) Sub-1-34 m/z = 508.02(C₃₀H₁₈BrClO = 509.83)Sub-1-35 m/z = 508.02(C₃₀H₁₈BrClO = 509.83) Sub-1-36 m/z =508.02(C₃₀H₁₈BrClO = 509.83) Sub-1-37 m/z = 508.02(C₃₀H₁₈BrClO = 509.83)Sub-1-38 m/z = 508.02(C₃₀H₁₈BrClO = 509.83) Sub-1-39 m/z =508.02(C₃₀H₁₈BrClO = 509.83) Sub-1-40 m/z = 508.02(C₃₀H₁₈BrClO = 509.83)Sub-1-41 m/z = 524.00(C₃₀H₁₈BrClS = 525.89) Sub-1-42 m/z =524.00(C₃₀H₁₈BrClS = 525.89) Sub-1-43 m/z = 508.02(C₃₀H₁₈BrClO = 509.83)Sub-1-44 m/z = 508.02(C₃₀H₁₈BrClO = 509.83) Sub-1-45 m/z =508.02(C₃₀H₁₈BrClO = 509.83) Sub-1-46 m/z = 508.02(C₃₀H₁₈BrClO = 509.83)Sub-1-47 m/z = 524.00(C₃₀H₁₈BrClS = 525.89) Sub-1-48 m/z =461.95(C₂₄H₁₂BrClOS = 463.77) Sub-1-49 m/z = 461.95(C₂₄H₁₂BrClOS =463.77) Sub-1-50 m/z = 477.93(C₂₄H₁₂BrClS₂ = 479.83) Sub-1-51 m/z =461.95(C₂₄H₁₂BrClOS = 463.77) Sub-1-52 m/z = 511.96(C₂₈H₁₄BrClOS =513.83) Sub-1-53 m/z = 461.95(C₂₄H₁₂BrClOS = 463.77) Sub-1-54 m/z =521.02(C₃₀H₁₇BrClNO = 522.83) Sub-1-55 m/z = 371.94(C₁₈H₁₀BrClS =373.69) Sub-1-56 m/z = 461.95(C₂₄H₁₂BrClOS = 463.77) Sub-1-57 m/z =596.05(C₃₇H₂₂BrClO = 597.94) Sub-1-58 m/z = 461.95(C₂₄H₁₂BrClOS =463.77) Sub-1-59 m/z = 534.04(C₃₂H₂₀BrClO = 535.87) Sub-1-60 m/z =461.95(C₂₄H₁₂BrClOS = 463.77) Sub-1-61 m/z = 445.97(C₂₄H₁₂BrClO₂ =447.71) Sub-1-62 m/z = 610.02(C₃₇H₂₀BrClS = 611.98) Sub-1-63 m/z =641.99(C₃₇H₂₀BrClS₂ = 644.04) Sub-1-64 m/z = 703.04(C₄₂H₂₃BrClNOS =705.07) Sub-1-65 m/z = 461.95(C₂₄H₁₂BrClOS = 463.77) Sub-1-66 m/z = 461.95(C₂₄H₁₂BrClOS = 463.77) Sub-1-67 m/z = 701.06(C₄₃H₂₅BrClNS = 703.09)Sub-1-68 m/z = 477.93(C₂₄H₁₂BrClS₂ = 479.83) Sub-1-69 m/z =612.03(C₃₇H₂₂BrClS = 614.00) Sub-1-70 m/z = 587.01(C₃₄H₁₉BrClNS =588.95) Sub-1-71 m/z = 477.93(C₂₄H₁₂BrClS₂ = 479.83) Sub-1-72 m/z =477.93(C₂₄H₁₂BrClS₂ = 479.83) Sub-1-73 m/z = 461.95(C₂₄H₁₂BrClOS =463.77) Sub-1-74 m/z = 477.93(C₂₄H₁₂BrClS₂ = 479.83) Sub-1-75 m/z =461.95(C₂₄H₁₂BrClOS = 463.77) Sub-1-76 m/z = 588.00(C₃₄H₁₈BrClOS =589.93) Sub-1-77 m/z = 434.98(C₂₁H₁₁BrClN₃O = 436.69) Sub-1-78 m/z =500.97(C₂₅H₁₃BrClN₃S = 502.81) Sub-1-79 m/z = 525.99(C₂₈H₁₆BrClN₂S =527.86) Sub-1-80 m/z = 526.99(C₂₇H₁₅BrClN₃S = 528.85) Sub-1-81 m/z =279.93(C₁₂H₆BrClO = 281.53) Sub-1-82 m/z = 279.93(C₁₂H₆BrClO = 281.53)Sub-1-83 m/z = 295.91(C₁₂H₆BrClS = 297.59) Sub-1-84 m/z =295.91(C₁₂H₆BrClS = 297.59) Sub-1-85 m/z = 371.94(C₁₈H₁₀BrClS = 373.69)Sub-1-86 m/z = 371.94(C₁₈H₁₀BrClS = 373.69) Sub-1-87 m/z =279.93(C₁₂H₆BrClO = 281.53) Sub-1-88 m/z = 497.98(C₂₈H₁₆BrClS = 499.85)Sub-1-89 m/z = 461.95(C₂₄H₁₂BrClOS = 463.77) Sub-1-90 m/z =295.91(C₁₂H₆BrClS = 297.59) Sub-1-91 m/z = 295.91(C₁₂H₆BrClS = 297.59)Sub-1-92 m/z = 295.91(C₁₂H₆BrClS = 297.59) Sub-1-93 m/z =481.86(C₁₈H₉BrClIO = 483.53) Sub-1-94 m/z = 481.86(C₁₈H₉BrClIO = 483.53)Sub-1-95 m/z = 497.83(C₁₈H₉BrClIS = 499.59) Sub-1-96 m/z =405.98(C₂₂H₁₂BrClO = 407.69) Sub-1-97 m/z = 481.86(C₁₈H₉BrClIO = 483.53)Sub-1-98 m/z = 371.94(C₁₈H₁₀BrClS = 373.69) Sub-1-99 m/z =497.83(C₁₈H₉BrClIS = 499.59) Sub-1-100 m/z = 531.87(C₂₂H₁₁BrClIO =533.59) Sub-1-101 m/z = 481.86(C₁₈H₉BrClIO = 483.53) Sub-1-102 m/z =481.86(C₁₈H₉BrClIO = 483.53) Sub-1-103 m/z = 524.00(C₃₀H₁₈BrClS =525.89) Sub-1-104 m/z = 547.85(C₂₂H₁₁BrClIS = 549.65) Sub-1-105 m/z =371.94(C₁₈H₁₀BrClS = 373.69) Sub-1-106 m/z = 433.87(C₁₈H₉Br₂ClO =436.53) Sub-1-107 m/z = 449.85(C₁₈H₉Br₂ClS = 452.59) Sub-1-108 m/z =483.89(C₂₂H₁₁Br₂ClO = 486.59) Sub-1-109 m/z = 355.96(C₁₈H₁₀BrClO =357.63) Sub-1-110 m/z = 279.93(C₁₂H₆BrClO = 281.53) Sub-1-111 m/z =355.96(C₁₈H₁₀BrClO = 357.63) Sub-1-112 m/z = 279.93(C₁₂H₆BrClO = 281.53)Sub-1-113 m/z = 295.91(C₁₂H₆BrClS = 297.59) Sub-1-114 m/z =295.91(C₁₂H₆BrClS = 297.59) Sub-1-115 m/z = 477.93(C₂₄H₁₂BrClS₂ =479.83) Sub-1-116 m/z = 295.91(C₁₂H₆BrClS = 297.59) Sub-1-117 m/z =279.93(C₁₂H₆BrClO = 281.53) Sub-1-118 m/z = 279.93(C₁₂H₆BrClO = 281.53)Sub-1-119 m/z = 329.94(C₁₆H₈BrClO = 331.59) Sub-1-120 m/z =279.93(C₁₂H₆BrClO = 281.53) Sub-1-121 m/z = 295.91(C₁₂H₆BrClS = 297.59)Sub-1-122 m/z = 295 .91(C₁₂H₆BrClS = 297.59) Sub-1-123 m/z =345.92(C₁₆H₈BrClS = 347.65) Sub-1-124 m/z = 345.92(C₁₆H₈BrClS = 347.65)Sub-1-125 m/z = 371.94(C₁₈H₁₀BrClS = 373.69) Sub-1-126 m/z =511.96(C₂₈H₁₄BrClOS = 513.83) Sub-1-127 m/z = 355.96(C₁₈H₁₀BrClO =357.63) Sub-1-128 m/z = 431.99(C₂₄H₁₄BrClO = 433.73) Sub-1-129 m/z =279.93(C₁₂H₆BrClO = 281.53) Sub-1-130 m/z = 295.91(C₁₂H₆BrClS = 297.59)Sub-1-131 m/z = 295.91(C₁₂H₆BrClS = 297.59) Sub-1-132 m/z =355.96(C₁₈H₁₀BrClO = 357.63) Sub-1-133 m/z = 295.91(C₁₂H₆BrClS = 297.59)Sub-1-134 m/z = 371.94(C₁₈H₁₀BrClS = 373.69) Sub-1-135 m/z =371.94(C₁₈H₁₀BrClS = 373.69)

II. Synthesis of Sub-2

Sub-2 of Scheme 1 is synthesized by the reaction route of Scheme 4below, but is not limited thereto. Hal⁶ is I, Br or Cl.

In Reaction Scheme 4, E and F are as defined in Scheme 1.

1. Synthesis Example of Sub-2-2

After placing Sub-2-a-2 (20.0 g, 177.7 mmol), Sub-2-b-2 (44.5 g, 177.7mmol), Pd₂(dba)₃ 4.9 g, 5.3 mmol), P(t-Bu)₃ (2.2 g, 10.7 mmol), NaOt-Bu(34.2 g, 355.4 mmol), toluene (888 mL) to a round-bottom flask, proceedwith the reaction at 80° C. When the reaction is complete, the mixtureis extracted with CH₂Cl₂ and water, and the organic layer is dried overMgSO₄ and concentrated. Then, the resulting organic material wasrecrystallized by silicagel column to obtain 45.3 g of a product. (yield76%)

2. Synthesis Example of Sub-2-3

Sub-2-a-2 (20.0 g, 177.7 mmol), Sub-2-b-3 (70.9 g, 177.7 mmol),Pd₂(dba)₃ (4.9 g, 5.3 mmol), P(t-Bu)₃ (2.2 g, 10.7 mmol), NaOt-Bu (34.2g, 355.4 mmol), toluene (888 mL) were tested in a round-bottom flask inthe same manner as in Sub-2-2 to obtain 30.0 g of the product. (Yield:77%)

3. Synthesis Example of Sub-2-94

Sub-2-a-94 (20.0 g, 83.8 mmol), Sub-2-b-2 (21.0 g, 83.8 mmol), Pd₂(dba)₃(2.3 g, 2.5 mmol), P(t-Bu)₃ (1.0 g, 5.0 mmol), NaOt-Bu (16.1 g, 167.6mmol), toluene (419 mL) were tested in a round-bottom flask in the samemanner as in Sub-2-2 to obtain 30.2 g of the product. (Yield: 78%)

4. Synthesis Example of Sub-2-96

Sub-2-a-96 (20.0 g, 63.5 mmol), Sub-2-b-2 (15.9 g, 63.5 mmol), Pd₂(dba)₃(1.8 g, 1.9 mmol), P(t-Bu)₃ (0.8 g, 3.8 mmol), NaOt-Bu (12.2 g, 127.1mmol), toluene (318 mL) were tested in a round-bottom flask in the samemanner as in Sub-2-2 to obtain 26.3 g of the product. (Yield: 77%)

5. Synthesis Example of Sub-2-114

Sub-2-a-2 (20.0 g, 177.7 mmol), Sub-2-b-114 (5.4 g, 60.3 mmol),Pd₂(dba)₃ (4.9 g, 5.3 mmol), P(t-Bu)₃ (2.2 g, 10.7 mmol), NaOt-Bu (34.2g, 355.4 mmol), toluene (888 mL) were tested in a round-bottom flask inthe same manner as in Sub-2-2 to obtain 56.4 g of the product. (Yield:79%)

6. Synthesis Example of Sub-2-156

Sub-2-a-156 (30.0 g, 88.4 mmol), Aniline (8.2 g, 88.4 mmol), Pd₂(dba)₃(2.43 g, 2.65 mmol), P(t-Bu)₃ (1.07 g, 5.31 mmol), NaOt-Bu (17.0 g, 177mmol), toluene (440 mL) were tested in a round-bottom flask in the samemanner as in Sub-2-2 to obtain 22.4 g of the product. (Yield: 72%)

7. Synthesis Example of Sub-2-159

Sub-2-a-159 (30.0 g, 88.4 mmol), Aniline (8.2 g, 88.4 mmol), Pd₂(dba)₃(2.43 g, 2.65 mmol), P(t-Bu)₃ (1.07 g, 5.31 mmol), NaOt-Bu (17.0 g, 177mmol), toluene (440 mL) were tested in a round-bottom flask in the samemanner as in Sub-2-2 to obtain 21.4 g of the product. (Yield: 69%)

8. Synthesis Example of Sub-2-162

Sub-2-a-162 (30.0 g, 92.8 mmol), Aniline (8.6 g, 92.8 mmol), Pd₂(dba)₃(2.55 g, 2.78 mmol), P(t-Bu)₃ (1.13 g, 5.57 mmol), NaOt-Bu (17.8 g, 186mmol), toluene (465 mL) were tested in a round-bottom flask in the samemanner as in Sub-2-2 to obtain 23.4 g of the product. (Yield: 75%)

The compound belonging to Sub-2 may be the following compounds, but isnot limited thereto, and Table 2 below shows FD-MS (FieldDesorption-Mass Spectrometry) values of the compounds belonging toSub-2.

TABLE 2 compound FD-MS compound FD-MS Sub-2-1 m/z = 169.09(C₁₂H₁₁N =169.23) Sub-2-2 m/z = 335.13(C₂₄H₁₇NO = 335.41) Sub-2-3 m/z =219.10(C₁₆H₁₃N = 219.29) Sub-2-4 m/z = 579.20(C₄₂H₂₉NS = 579.76) Sub-2-5m/z = 351.11(C₂₄H₁₇NS = 351.47) Sub-2-6 m/z = 245.12(C₁₈H₁₅N = 245.33)Sub-2-7 m/z = 517.15(C₃₆H₂₃NOS = 517.65) Sub-2-8 m/z = 411.16(C₃₀H₂₁NO =411.5) Sub-2-9 m/z = 591.20(C₄₃H₂₉NS = 591.77) Sub-2-10 m/z =427.14(C₃₀H₂₁NS = 427.57) Sub-2-11 m/z = 605.18(C₄₃H₂₇NOS = 605.76)Sub-2-12 m/z = 397.18(C₃₀H₂₃N = 397.52) Sub-2-13 m/z = 301.18(C₂₂H₂₃N =301.43) Sub-2-14 m/z = 259.10(C₁₈H₁₃NO = 259.31) Sub-2-15 m/z =351.11(C₂₄H₁₇NS = 351.47) Sub-2-16 m/z = 501.17(C₃₆H₂₃NO₂ = 501.59)Sub-2-17 m/z = 565.17(C₄₀H₂₃NO₃ = 565.63) Sub-2-18 m/z = 335.13(C₂₄H₁₇NO= 335.41) Sub-2-19 m/z = 590.20(C₄₂H₂₆N₂O₂ = 590.68) Sub-2-20 m/z =309.12(C₂₂H₁₅NO = 309.37) Sub-2-21 m/z = 286.11(C₁₉H₁₄N₂O = 286.33)Sub-2-22 m/z = 605.18(C₄₃H₂₇NOS = 605.76) Sub-2-23 m/z = 371.17(C₂₈H₂₁N= 371.48) Sub-2-24 m/z = 385.15(C₂₈H₁₉NO = 385.47) Sub-2-25 m/z =501.17(C₃₆H₂₃NO₂ = 501.59) Sub-2-26 m/z = 487.19(C₃₆H₂₅NO = 487.60)Sub-2-27 m/z = 334.15(C₂₄H₁₈N₂ = 334.42) Sub-2-28 m/z = 295.14(C₂₂H₁₇N =295.39) Sub-2-29 m/z = 365.09(C₂₄H₁₅NOS = 365.45) Sub-2-30 m/z =591.20(C₄₃H₂₉NS = 591.77) Sub-2-31 m/z = 439.14(C₃₁H₂₁NS = 439.58)Sub-2-32 m/z = 566.18(C₄₀H₂₆N₂S = 566.72) Sub-2-33 m/z = 335.13(C₂₄H₁₇NO= 335.41) Sub-2-34 m/z = 401.12(C₂₈H₁₉NS = 401.53) Sub-2-35 m/z =275.08(C₁₈H₁₃NS = 275.37) Sub-2-36 m/z = 457.10(C₃₀H₁₉NS₂ = 457.61)Sub-2-37 m/z = 401.21(C₃₀H₂₇N = 401.55) Sub-2-38 m/z = 451.19(C₃₃H₂₅NO =451.57) Sub-2-39 m/z = 397.18(C₃₀H₂₃N = 397.52) Sub-2-40 m/z =511.19(C₃₈H₂₅NO = 511.62) Sub-2-41 m/z = 435.16(C₃₂H₂₁NO = 435.53)Sub-2-42 m/z = 452.15(C₃₁H₂₀N₂O₂ = 452.51) Sub-2-43 m/z = 219.10(C₁₆H₁₃N= 219.29) Sub-2-44 m/z = 527.17(C₃₈H₂₅NS = 527.69) Sub-2-45 m/z =503.17(C₃₆H₂₅NS = 503.66) Sub-2-46 m/z = 356.14(C₂₄H₁₂D₅NS = 356.5)Sub-2-47 m/z = 205.07(C₁₂H₉F₂N = 205.21) Sub-2-48 m/z = 365.14(C₂₅H₁₉NO₂= 365.43) Sub-2-49 m/z = 195.10(C₁₄H₁₃N = 195.27) Sub-2-50 m/z =411.16(C₃₀H₂₁NO = 411.50) Sub-2-51 m/z = 475.16(C₃₄H₂₁NO₂ = 475.55)Sub-2-52 m/z = 245.12(C₁₈H₁₅N = 245.33) Sub-2-53 m/z = 435.16(C₃₂H₂₁NO =435.53) Sub-2-54 m/z = 617.18(C₄₄H₂₇NOS = 617.77) Sub-2-55 m/z =340.16(C₂₄H₁₂D₅NO = 340.44) Sub-2-56 m/z = 309.12(C₂₂H₁₅NO = 309.37)Sub-2-57 m/z = 577.20(C₄₂H₂₇NO₂ = 577.68) Sub-2-58 m/z = 407.17(C₃₁H₂₁N= 407.52) Sub-2-59 m/z = 501.21(C₃₇H₂₇NO = 501.63) Sub-2-60 m/z =334.15(C₂₄H₁₈N₂ = 334.42) Sub-2-61 m/z = 427.14(C₃₀H₂₁NS = 427.57)Sub-2-62 m/z = 450.21(C₃₃H₂₆N₂ = 450.59) Sub-2-63 m/z = 441.12(C₃₀H₁₉NOS= 441.55) Sub-2-64 m/z = 334.15(C₂₄H₁₈N₂ = 334.42) Sub-2-65 m/z =371.17(C₂₈H₂₁N = 371.48) Sub-2-66 m/z = 269.12(C₂₀H₁₅N = 269.35)Sub-2-67 m/z = 371.17(C₂₈H₂₁N = 371.48) Sub-2-68 m/z = 537.21(C₄₀H₂₇NO =537.66) Sub-2-69 m/z = 385.15(C₂₈H₁₉NO = 385.47) Sub-2-70 m/z =401.12(C₂₈H₁₉NS = 401.53) Sub-2-71 m/z = 543.20(C₃₉H₂₉NS = 543.73)Sub-2-72 m/z = 245.12(C₁₈H₁₅N = 245.33) Sub-2-73 m/z = 411.20(C₃₁H₂₅N =411.55) Sub-2-74 m/z = 371.17(C₂₈H₂₁N = 371.48) Sub-2-75 m/z =451.14(C₃₂H₂₁NS = 451.59) Sub-2-76 m/z = 259.04(C₁₂H₆F₅N = 259.18)Sub-2-77 m/z = 477.16(C₃₄H₂₃NS = 477.63) Sub-2-78 m/z = 269.12(C₂₀H₁₅N =269.35) Sub-2-79 m/z = 501.16(C₃₆H₂₃NS = 501.65) Sub-2-80 m/z =319.14(C₂₄H₁₇N = 319.41) Sub-2-81 m/z = 483.20(C₃₇H₂₅N = 483.61)Sub-2-82 m/z = 498.21(C₃₇H₂₆N₂ = 498.63) Sub-2-83 m/z = 251.17(C₁₈H₂₁N =251.37) Sub-2-84 m/z = 250.15(C₁₈H₁₀D₅N = 250.36) Sub-2-85 m/z =391.19(C₂₈H₂₅NO = 391.51) Sub-2-86 m/z = 639.20(C₄₇H₂₉NS = 639.82)Sub-2-87 m/z = 321.15(C₂₄H₁₉N = 321.42) Sub-2-88 m/z = 400.17(C₂₇H₂₀N₄ =400.49) Sub-2-89 m/z = 477.16(C₃₄H₂₃NS = 477.63) Sub-2-90 m/z =321.15(C₂₄H₁₉N = 321.42) Sub-2-91 m/z = 321.15(C₂₄H₁₉N = 321.42)Sub-2-92 m/z = 423.16(C₃₁H₂₁NO = 423.52) Sub-2-93 m/z = 503.17(C₃₆H₂₅NS= 503.66) Sub-2-94 m/z = 461.18(C₃₄H₂₃NO = 461.56) Sub-2-95 m/z =309.12(C₂₂H₁₅NO = 309.37) Sub-2-96 m/z = 537.21(C₄₀H₂₇NO = 537.66)Sub-2-97 m/z = 457.18(C₃₅H₂₃N = 457.58) Sub-2-98 m/z = 487.19(C₃₆H₂₅NO =487.60) Sub-2-99 m/z = 411.16(C₃₀H₂₁NO = 411.5) Sub-2-100 m/z =503.17(C₃₆H₂₅NS = 503.66) Sub-2-101 m/z = 369.15(C₂₈H₁₉N = 369.47)Sub-2-102 m/z = 365.09(C₂₄H₁₅NOS = 365.45) Sub-2-103 m/z =349.11(C₂₄H₁₅NO₂ = 349.39) Sub-2-104 m/z = 503.17(C₃₆H₂₅NS = 503.66)Sub-2-105 m/z = 437.21(C₃₃H₂₇N = 437.59) Sub-2-106 m/z = 461.18(C₃₄H₂₃NO= 461.56) Sub-2-107 m/z = 371.17(C₂₆H₂₁N = 371.48) Sub-2-108 m/z =537.21(C₄₀H₂₇NO = 537.66) Sub-2-109 m/z = 485.22(C₃₄H₃₁NS = 485.69)Sub-2-110 m/z = 291.07(C₁₈H₁₃NOS = 291.37) Sub-2-111 m/z =275.09(C₁₈H₁₃NO₂ = 275.31) Sub-2-112 m/z = 516.18(C₃₆H₂₄N₂O₂ = 516.60)Sub-2-113 m/z = 425.19(C₃₀H₂₃N₃ = 425.54) Sub-2-114 m/z =401.12(C₂₈H₁₉NS = 401.53) Sub-2-115 m/z = 561.25(C₄₃H₃₁N = 561.73)Sub-2-116 m/z = 727.29(C₅₅H₃₇NO = 727.91) Sub-2-117 m/z =423.16(C₃₁H₂₁NO = 423.52) Sub-2-118 m/z = 517.15(C₃₆H₂₃NOS = 517.65)Sub-2-119 m/z = 477.16(C₃₄H₂₃NS = 477.63) Sub-2-120 m/z =351.11(C₂₄H₁₇NS = 351.47) Sub-2-121 m/z = 335.13(C₂₄H₁₇NO = 335.41)Sub-2-122 m/z = 577.20(C₄₂H₂₇NO₂ = 577.68) Sub-2-123 m/z =359.13(C₂₆H₁₇NO = 359.43) Sub-2-124 m/z = 698.19(C₄₈H₃₀N₂S₂ = 698.90)Sub-2-125 m/z = 427.14(C₃₀H₂₁NS = 427.57) Sub-2-126 m/z = 345.15(C₂₆H₁₉N= 345.45) Sub-2-127 m/z = 347.17(C₂₆H₂₁N = 347.46) Sub-2-128 m/z =576.22(C₄₂H₂₆N₂O = 576.70) Sub-2-129 m/z = 669.21(C₄₆H₃₁NOS = 669.84)Sub-2-130 m/z = 286.11(C₁₉H₁₄N₂O = 286.33) Sub-2-131 m/z =487.19(C₃₆H₂₅NO = 487.60) Sub-2-132 m/z = 285.15(C₂₁H₁₉N = 285.39)Sub-2-133 m/z = 461.18(C₃₄H₂₃NO = 461.56) Sub-2-134 m/z =601.20(C₄₄H₂₇NO₂ = 601.71) Sub-2-135 m/z = 409.18(C₃₁H₂₃N = 409.53)Sub-2-136 m/z = 335.13(C₂₄H₁₇NO = 335.41) Sub-2-137 m/z =487.19(C₃₆H₂₅NO = 487.60) Sub-2-138 m/z = 351.11(C₂₄H₁₇NS = 351.47)Sub-2-139 m/z = 639.20(C₄₇H₂₉NS = 639.82) Sub-2-140 m/z =351.11(C₂₄H₁₇NS = 351.47) Sub-2-141 m/z = 345.15(C₂₆H₁₉N = 345.45)Sub-2-142 m/z = 401.12(C₂₆H₁₉NS = 401.53) Sub-2-143 m/z =351.11(C₂₄H₁₇NS = 351.47) Sub-2-144 m/z = 639.11(C₄₂H₂₅NS₃ = 639.85)Sub-2-145 m/z = 553.19(C₄₀H₂₇NS = 553.72) Sub-2-146 m/z =401.12(C₂₈H₁₉NS = 401.53) Sub-2-147 m/z = 401.12(C₂₈H₁₉NS = 401.53)Sub-2-145 m/z = 435.16(C₃₂H₂₁NO = 435.53) Sub-2-149 m/z = 269.12(C₂₀H₁₅N= 269.35) Sub-2-150 m/z = 325.09(C₂₂H₁₅NS = 325.43) Sub-2-151 m/z =491.13(C₃₄H₂₁NOS = 491.61) Sub-2-152 m/z = 581.14(C₄₀H₂₃NO₂S = 581.69)Sub-2-153 m/z = 179.15(C₁₂HD₁₀N = 179.29) Sub-2-154 m/z =205.07(C₁₂H₉F₂N = 205.21) Sub-2-155 m/z = 225.15(C₁₆H₁₉N = 225.34)Sub-2-156 m/z = 351.11(C₂₄H₁₇NS = 351.47) Sub-2-157 m/z =351.11(C₂₄H₁₇NS = 351.47) Sub-2-158 m/z = 351.11(C₂₄H₁₇NS = 351.47)Sub-2-159 m/z = 351.11(C₂₄H₁₇NS = 351.47) Sub-2-160 m/z =427.14(C₃₀H₂₁NS = 427.57) Sub-2-161 m/z = 335.13(C₂₄H₁₇NO = 335.41)Sub-2-162 m/z = 335.13(C₂₄H₁₇NO = 335.41) Sub-2-163 m/z =335.13(C₂₄H₁₇NO = 335.41) Sub-2-164 m/z = 335.13(C₂₄H₁₇NO = 335.41)Sub-2-165 m/z = 411.16(C₃₀H₂₁NO = 411.50)

III. Synthesis of Final Product 1. Synthesis Example of P-1

(1) Synthesis of Inter-1-1

After placing Sub-1-1 (20.0 g, 55.9 mmol), Sub-2-1 (9.1 g, 55.9 mmol),Pd₂(dba)₃ (1.5 g, 1.7 mmol), P(t-Bu)₃ (0.7 g, 3.4 mmol), NaOt-Bu (10.7g, 111.8 mmol), toluene (280 mL) to a round-bottom flask, proceed withthe reaction at 80° C. When the reaction is complete, the mixture isextracted with CH₂Cl₂ and water, and the organic layer is dried overMgSO₄ and concentrated. Then, the resulting organic material wasrecrystallized by silicagel column to obtain 17.5 g of a product. (yield70%)

(2) Synthesis of P-1

After placing Inter-1-1 (10.0 g, 22.4 mmol), Sub-2-2 (7.3 g, 22.4 mmol),Pd₂(dba)₃ (0.6 g, 0.7 mmol), P(t-Bu)₃ (0.3 g, 1.4 mmol), NaOt-Bu (4.3 g,44.8 mmol), toluene (112 mL) into a round-bottom flask, 10.3 g of theproduct was obtained by performing an experiment at 80° C. in the samemanner as Inter-1-1. (Yield: 71%)

2. Synthesis Example of P-2

(1) Synthesis of Inter-1-2

After placing Sub-1-2 (20.0 g, 49.1 mmol), Sub-2-3 (10.4 g, 49.1 mmol),Pd₂(dba)₃ (1.4 g, 1.5 mmol), P(t-Bu)₃ (0.6 g, 2.9 mmol), NaOt-Bu (9.4 g,98.1 mmol), and toluene (245 mL) in a round-bottom flask, 18.2 g of theproduct was obtained by performing an experiment in the same manner asInter-1-1 above at 80° C. (Yield: 68%)

(2) Synthesis of P-2

After placing Inter-1-2 (10.0 g, 18.3 mmol), Sub-2-2 (5.9 g, 18.3 mmol),Pd₂(dba)₃ (0.5 g, 0.6 mmol), P(t-Bu)₃ (0.2 g, 1.1 mmol), NaOt-Bu (3.5 g,36.6 mmol), toluene (92 mL) in a round-bottom flask, 10.5 g of theproduct was obtained by performing an experiment in the same manner asInter-1-1 above at 80° C. (Yield: 68%)

3. Synthesis Example of P-49

(1) Synthesis of Inter-1-49

After placing Sub-1-49 (10.0 g, 21.6 mmol), Sub-2-1 (3.6 g, 21.6 mmol),Pd₂(dba)₃ (0.59 g, 0.65 mmol), P(t-Bu)₃ (0.26 g, 1.29 mmol), NaOt-Bu(4.1 g, 43.1 mmol), toluene (108 mL) in a round-bottom flask, 8.5 g ofthe product was obtained by performing an experiment in the same manneras Inter-1-1 above at 80° C. (Yield: 71%)

(2) Synthesis of P-49

After placing Inter-1-49 (8.5 g, 15.3 mmol), Sub-2-50 (6.3 g, 15.3mmol), Pd₂(dba)₃ (0.42 g, 0.46 mmol), P(t-Bu)₃ (0.19 g, 0.92 mmol),NaOt-Bu (2.9 g, 30.6 mmol), toluene (77 mL) in a round-bottom flask,10.2 g of the product was obtained by performing an experiment in thesame manner as Inter-1-1 above at 80° C. (Yield: 72%)

4. Synthesis Example of P-55

(1) Synthesis of Inter-1-55

After placing Sub-1-55 (20.0 g, 53.5 mmol), Sub-2-1 (8.8 g, 53.5 mmol),Pd₂(dba)₃ (1.5 g, 1.6 mmol), P(t-Bu)₃ (0.7 g, 3.2 mmol), NaOt-Bu (10.3g, 107.0 mmol), toluene (268 mL) in a round-bottom flask, 17.6 g of theproduct was obtained by performing an experiment in the same manner asInter-1-1 above at 80° C. (Yield: 71%)

(2) Synthesis of P-55

After placing Inter-1-55 (10.0 g, 21.6 mmol), Sub-2-2 (7.0 g, 21.6mmol), Pd₂(dba)₃ (0.6 g, 0.7 mmol), P(t-Bu)₃ (0.3 g, 1.3 mmol), NaOt-Bu(4.2 g, 43.3 mmol), toluene (108 mL) in a round-bottom flask, 11.9 g ofthe product was obtained by performing an experiment in the same manneras Inter-1-1 above at 80° C. (Yield: 72%)

5. Synthesis Example of P-83

(1) Synthesis of Inter-1-83

After placing Sub-1-83 (20.0 g, 67.2 mmol), Sub-2-1 (11.6 g, 25.9 mmol),Pd₂(dba)₃ (1.9 g, 2.0 mmol), P(t-Bu)₃ (0.8 g, 4.0 mmol), NaOt-Bu (12.9g, 134.4 mmol), toluene (336 mL) in a round-bottom flask, 17.4 g of theproduct was obtained by performing an experiment in the same manner asInter-1-1 above at 80° C. (Yield: 67%)

(2) Synthesis of P-83

After placing Inter-1-83 (10.0 g, 25.9 mmol), Sub-2-94 (11.6 g, 25.9mmol), Pd₂(dba)₃ (0.7 g, 0.8 mmol), P(t-Bu)₃ (0.3 g, 1.6 mmol), NaOt-Bu(5.0 g, 51.8 mmol), toluene (130 mL) in a round-bottom flask, 14.5 g ofthe product was obtained by performing an experiment in the same manneras Inter-1-1 above at 80° C. (Yield: 69%)

6. Synthesis Example of P-97

(1) Synthesis of Inter-1-97

After placing Sub-1-97 (20.0 g, 41.4 mmol), Sub-2-114 (16.0 g, 41.4mmol), Pd₂(dba)₃ (1.1 g, 1.2 mmol), P(t-Bu)₃ (0.5 g, 2.5 mmol), NaOt-Bu(8.0 g, 82.7 mmol), toluene (207 mL) in a round-bottom flask, 22.5 g ofthe product was obtained by performing an experiment in the same manneras Inter-1-1 above at 80° C. (Yield: 72%)

(2) Synthesis of P-2-97

After placing Inter-1-97 (15.0 g, 19.8 mmol), Sub-2-1 (3.2 g, 19.8mmol), Pd₂(dba)₃ (0.5 g, 0.6 mmol), P(t-Bu)₃ (0.2 g, 1.2 mmol), NaOt-Bu(3.8 g, 39.6 mmol), toluene (99 mL) in a round-bottom flask, 12.6 g ofthe product was obtained by performing an experiment in the same manneras Inter-1-1 above at 80° C. (Yield: 75%)

(3) Synthesis of P-97

After placing Inter-2-97 (10.0 g, 11.8 mmol), Sub-2-5 (4.0 g, 11.8mmol), Pd₂(dba)₃ (0.3 g, 0.4 mmol), P(t-Bu)₃ (0.1 g, 0.7 mmol), NaOt-Bu(2.3 g, 23.7 mmol), toluene (59 mL) in a round-bottom flask, 9.7 g ofthe product was obtained by performing an experiment in the same manneras Inter-1-1 above at 80° C. (Yield: 71%)

7. Synthesis Example of P-129

(1) Synthesis of Inter-1-129

After placing Sub-1-112 (10.0 g, 35.5 mmol), Sub-2-162 (11.9 g, 35.5mmol), Pd₂(dba)₃ (0.98 g, 1.07 mmol), P(t-Bu)₃ (0.43 g, 2.13 mmol),NaOt-Bu (6.8 g, 71.0 mmol), toluene (178 mL) in a round-bottom flask,14.1 g of the product was obtained by performing an experiment in thesame manner as Inter-1-1 above at 80° C. (Yield: 74%)

(2) Synthesis of P-129

After placing Inter-1-129 (14.1 g, 26.3 mmol), Sub-2-1 (4.4 g, 26.3mmol), Pd₂(dba)₃ (0.72 g, 0.79 mmol), P(t-Bu)₃ (0.32 g, 1.58 mmol),NaOt-Bu (5.1 g, 52.6 mmol), toluene (131 mL) in a round-bottom flask,12.3 g of the product was obtained by performing an experiment in thesame manner as Inter-1-1 above at 80° C. (Yield: 70%)

8. Synthesis Example of P-133

(1) Synthesis of Inter-1-133

After placing Sub-1-131 (40.0 g, 134 mmol), Sub-2-1 (22.7 g, 134 mmol),Pd₂(dba)₃ (3.69 g, 4.03 mmol), P(t-Bu)₃ (1.63 g, 8.06 mmol), NaOt-Bu(25.8 g, 269 mmol), toluene (672 mL) in a round-bottom flask, 40.5 g ofthe product was obtained by performing an experiment in the same mannersInter-1-1 above at 80° C. (Yield: 78%)

(2) Synthesis of P-133

After placing Inter-1-133 (15.0 g, 38.9 mmol), Sub-2-2 (13.0 g, 38.9mmol), Pd₂(dba)₃ (1.07 g, 1.17 mmol), P(t-Bu)₃ (0.47 g, 2.33 mmol),NaOt-Bu (7.5 g, 77.7 mmol), toluene (194 mL) in a round-bottom flask,19.4 g of the product was obtained by performing an experiment in thesame manner as Inter-1-1 above at 80° C. (Yield: 73%)

9. Synthesis Example of P-134

(1) Synthesis of Inter-1-134

After placing Sub-1-125 (10.0 g, 26.8 mmol), Sub-2-1 (4.5 g, 26.8 mmol),Pd₂(dba)₃ (0.74 g, 0.80 mmol), P(t-Bu)₃ (0.32 g, 1.61 mmol), NaOt-Bu(5.1 g, 53.5 mmol), toluene (134 mL) in a round-bottom flask, 8.4 g ofthe product was obtained by performing an experiment in the same manneras Inter-1-1 above at 80° C. (Yield: 68%)

(2) Synthesis of P-134

After placing Inter-1-134 (8.4 g, 18.2 mmol), Sub-2-2 (6.1 g, 18.2mmol), Pd₂(dba)₃ (0.50 g, 0.55 mmol), P(t-Bu)₃ (0.22 g, 1.09 mmol),NaOt-Bu (3.5 g, 36.4 mmol), toluene (91 mL) in a round-bottom flask, 9.3g of the product was obtained by performing an experiment in the samemanner as Inter-1-1 above at 80° C. (Yield: 67%)

10. Synthesis Example of P-150

After placing Inter-1-133 (25.0 g, 64.8 mmol), Sub-2-5 (22.8 g, 64.8mmol), Pd₂(dba)₃ (1.78 g, 1.94 mmol), P(t-Bu)₃ (0.79 g, 3.89 mmol),NaOt-Bu (12.5 g, 130 mmol), toluene (324 mL) in a round-bottom flask,33.1 g of the product was obtained by performing an experiment in thesame manner as Inter-1-1 above at 80° C. (Yield: 73%)

11. Synthesis Example of P-152

The obtained P-150 (15.0 g, 21.4 mmol) was dissolved in perdeuteratedbenzene (C₆D6) (161.8 g, 1926 mmol) and CF₃SO₃D (16.1 g, 107 mmol) wasadded, and then reacted at 80° C. for 3 hours and formed a deuteratedmaterial. Periodically take a sample and measure the degree of deuteriumby LC-MS. After the deuterium exchange reaction is completed at adesired substitution rate, cool to room temperature, quenching by addingNa₂CO₃ in D₂O, and concentrate the organic solvent. Recrystallizationusing toluene and acetone solvent gave 14.1 g (yield: 90%) of deuteratedcompound P-152. The final mass was determined by LC-MS to confirm thatit was 85.2% deuterated.

Meanwhile, the ED-MS values of the compounds P-1 to P-152 of the presentinvention prepared according to the above synthesis examples are shownin Table 3 below.

TABLE 3 compound FD-MS compound FD-MS P-1 m/z = 744.28(C₅₄H₃₆N₂O₂ =744.89) P-2 m/z = 844.31(C₆₂H₄₀N₂O₂ = 845.01) P-3 m/z =820.31(C₆₀H₄₀N₂O₂ = 820.99) P-4 m/z = 870.32(C₆₄H₄₂N₂O₂ = 871.05) P-5m/z = 852.26(C₆₀H₄₀N₂S₂ = 853.11) P-6 m/z = 852.26(C₆₀H₄₀N₂S₂ = 853.11)P-7 m/z = 852.26(C₆₀H₄₀N₂S₂ = 853.11) P-8 m/z = 928.29(C₆₆H₄₄N₂S₂ =929.21) P-9 m/z = 1090.36(C₇₉H₅₀N₂O₂S = 1091.34) P-10 m/z =1000.35(C₇₃H₄₈N₂OS = 1001.26) P-11 m/z = 942.27(C₆₆H₄₂N₂OS₂ = 943.20)P-12 m/z = 1179.39(C₈₅H₅₃N₃O₂S = 1180.44) P-13 m/z = 866.24(C₆₀H₃₈N₂OS₂= 867.10) P-14 m/z = 915.30(C₆₃H₄₁N₅OS = 916.12) P-15 m/z =998.33(C₇₃H₄₆N₂OS = 999.24) P-16 m/z = 860.29(C₆₂H₄₀N₂OS = 861.08) P-17m/z = 892.35(C₆₄H₄₈N₂OS = 893.16) P-18 m/z = 850.27(C₆₀H₃₈N₂O₂S =851.04) P-19 m/z = 942.27(C₆₆H₄₂N₂OS₂ = 943.20) P-20 m/z =976.31(C₇₀H₄₄N₂O₂S = 977.19) P-21 m/z = 810.27(C₅₈H₃₈N₂OS = 811.02) P-22m/z = 1002.33(C₇₂H₄₆N₂O₂S = 1003.23) P-23 m/z = 1091.35(C₇₈H₄₉N₃O₂S =1092.33) P-24 m/z = 960.34(C₇₀H₄₄N₂O₃ = 961.13) P-25 m/z =1066.32(C₇₆H₄₆N₂O₃S = 1067.28) P-26 m/z = 953.31(C₆₇H₄₃N₃O₂S = 954.16)P-27 m/z = 1090.36(C₇₉H₅₀N₂O₂S = 1091.34) P-28 m/z = 1088.38(C₈₀H₅₂N₂OS= 1089.37) P-29 m/z = 1002.33(C₇₂H₄₆N₂O₂S = 1003.23) P-30 m/z =1114.40(C₈₂H₅₄N₂OS = 1115.41) P-31 m/z = 1077.38(C₇₈H₅₁N₃OS = 1078.35)P-32 m/z = 1108.32(C₇₈H₄₈N₂O₂S₂ = 1109.37) P-33 m/z = 1152.41(C₈₅H₅₆N₂OS= 1153.46) P-34 m/z = 1397.44(C₁₀₁H₆₃N₃OS₂ = 1398.76) P-35 m/z =1128.37(C₈₂H₅₂N₂O₂S = 1129.39) P-36 m/z = 1124.29(C₇₈H₄₈N₂OS₃ = 1125.44)P-37 m/z = 1128.47(C₈₄H₆₀N₂O₂ = 1129.42) P-38 m/z = 1012.40(C₇₅H₅₂N₂O₂ =1013.25) P-39 m/z = 1124.43(C₈₄H₅₆N₂O₂ = 1125.38) P-40 m/z =1072.40(C₈₀H₅₂N₂O₂ = 1073.31) P-41 m/z = 1012.35(C₇₄H₄₈N₂OS = 1013.27)P-42 m/z = 1029.34(C₇₃H₄₇N₃O₂S = 1030.26) P-43 m/z = 1138.40(C₈₄H₅₄N₂OS= 1139.43) P-44 m/z = 1064.38(C₇₈H₅₂N₂OS = 1065.35) P-45 m/z =917.35(C₆₆H₃₉D₅N₂OS = 918.18) P-46 m/z = 932.32(C₆₆H₄₂F₂N₂O₂ = 933.07)P-47 m/z = 942.33(C₆₇H₄₆N₂O₂S = 943.18) P-48 m/z = 876.28(C₆₂H₄₀N₂O₂S =877.07) P-49 m/z = 926.30(C₆₆H₄₂N₂O₂S = 927.13) P-50 m/z =1006.27(C₇₀H₄₂N₂O₂S₂ = 1007.24) P-51 m/z = 1018.31(C₇₂H₄6N₂OS₂ =1019.29) P-52 m/z = 1182.33(C₈₄H₅₀N₂O₂S₂ = 1183.46) P-53 m/z =995.32(C₇₀H₃₇D₅N₂O₃S = 996.21) P-54 m/z = 115.41(C₈₄H₅₃N₃O₃ = 1152.37)P-55 m/z = 760.25(C₅₄H₃₆N₂OS = 760.96) P-56 m/z = 1254.42(C₉₂H₅₈N₂O₂S =1255.55) P-57 m/z = 1241.44(C₉₁H₅₉N₃OS = 1242.55) P-58 m/z =1147.36(C₈₁H₅₃N₃OS₂ = 1148.46) P-59 m/z = 1028.34(C₇₄H₄₈N₂O₂S = 1029.27)P-60 m/z = 1015.32(C₇₂H₄₅N₃O₂S = 1016.23) P-61 m/z = 1052.34(C₇₆H₄₈N₂O₂S= 1053.29) P-62 m/z = 1402.49(C₁₀₅H₆₆N₂OS = 1403.76) P-63 m/z =1180.35(C₈₅H₅₂N₂OS₂ = 1181.48) P-64 m/z = 1157.35(C₈₂H₅₁N₃OS₂ = 1158.45)P-65 m/z = 1134.37(C₈₁H₅₄N₂OS₂ = 1135.46) P-66 m/z = 1108.35(C₇₉H₅₂N₂OS₂= 1109.42) P-67 m/z = 1407.46(C₁₀₃H₆₅N₃S₂ = 1408.79) P-68 m/z =1098.22(C₇₀H₃₉F₅N₂S₃ = 1099.27) P-69 m/z = 1266.40(C₉₃H₅₈N₂S₂ = 1267.62)P-70 m/z = 1141.35(C₈₂H₅₁N₃S₂ = 1142.45) P-71 m/z = 1196.33(C₈₅H₅₂N₂S₃ =1197.55) P-72 m/z = 1211.34(C₈₅H₅₃N₃S₃ = 1212.56) P-73 m/z =932.34(C₆₆H₄₈N₂O₂S = 933.18) P-74 m/z = 1003.37(C₇₀H₄₅D₅N₂OS₂ = 1004.33)P-75 m/z = 1154.34(C₈₃H₅₀N₂OS₂ = 1155.45) P-76 m/z = 1144.35(C₈₂H₅₂N₂OS₂= 1145.45) P-77 m/z = 839.27(C₅₇H₃₇N₅OS = 840.02) P-78 m/z =1120.37(C₇₆H₄₈N₈OS = 1121.34) P-79 m/z = 1066.37(C₇₆H₅₀N₄OS = 1067.32)P-80 m/z = 1003.33(C₇₀H₄₅N₅OS = 1004.22) P-81 m/z = 810.27(C₅₈H₃₈N₂OS =811.02) P-82 m/z = 886.30(C₆₄H₄₂N₂OS = 887.11) P-83 m/z =810.27(C₅₈H₃₈N₂OS = 811.02) P-84 m/z = 1026.33(C₇₄H₄₆N₂O₂S = 1027.25)P-85 m/z = 1124.38(C₈₃H₅₂N₂OS = 1125.40) P-86 m/z = 836.29(C₆₀H₄₀N₂OS =837.05) P-87 m/z = 1032.28(C₇₂H₄₄N₂O₂S₂ = 1033.28) P-88 m/z =1016.31(C₇₂H₄₄N₂O₃S = 1017.22) P-89 m/z = 850.27(C₆₀H₃₈N₂O₂S = 851.04)P-90 m/z = 884.29(C₆₄H₄₀N₂OS = 885.10) P-91 m/z = 884.29(C₆₄H₄₀N₂OS =885.10) P-92 m/z = 1088.38(C₈₀H₅₂N₂OS = 1089.37) P-93 m/z =1183.42(C₈₂H₆₁N₃O₂S₂ = 1184.53) P-94 m/z = 1033.33(C₇₂H₄₇N₃O₃S =1034.25) P-95 m/z = 1108.38(C₇₈H₅₂N₄O₂S = 1109.36) P-96 m/z =1066.37(C₇₆H₅₀N₄OS = 1067.32) P-97 m/z = 1159.36(C₈₂H₅₃N₃OS₂ = 1160.47)P-98 m/z = 1152.41(C₈₅H₅₆N₂OS = 1153.46) P-99 m/z = 1319.48(C₉₇H₆₅N₃OS =1320.67) P-100 m/z = 1285.41(C₉₂H₅₉N₃OS₂ = 1286.62) P-101 m/z =1215.44(C₈₉H₅₇N₃O₃ = 1216.45) P-102 m/z = 1077.39(C₇₈H₅₁N₃O₃ = 1078.28)P-103 m/z = 1154.39(C₈₄H₅₄N₂O₂S = 1155.43) P-104 m/z =1530.44(C₁₀₈H₆₆N₄OS₃ = 1531.92) P-105 m/z = 852.26(C₆₀H₄₀N₂S₂ = 853.11)P-106 m/z = 1103.39(C₈₀H₅₃N₃OS = 1104.38) P-107 m/z = 1346.50(C₉₈H₆₆N₄OS= 1347.69) P-108 m/z = 1295.45(C₉₄H₆₁N₃O₂S = 1296.60) P-109 m/z =1013.36(C₇₃H₄₇N₃O₃ = 1014.20) P-110 m/z = 910.36(C₆₇H₄₆N₂O₂ = 911.12)P-111 m/z = 1010.35(C₇₄H₄₆N₂O₃ = 1011.19) P-112 m/z = 908.34(C₆₇H₄₄N₂O₂= 909.10) P-113 m/z = 852.26(C₆₀H₄₀N₂S₂ = 853.11) P-114 m/z =988.29(C₇₁H₄₄N₂S₂ = 989.27) P-115 m/z = 882.22(C₆₀H₃₈N₂S₃ = 883.16)P-116 m/z = 1170.23(C₇₈H₄₆N₂S₅ = 1171.54) P-117 m/z = 910.30(C₆₆H₄₂N₂OS= 911.14) P-118 m/z = 886.30(C₆₄H₄₂N₂OS = 887.11) P-119 m/z =784.25(C₅₆H₃₆N₂OS = 784.98) P-120 m/z = 734.24(C₅₂H₃₄N₂OS = 734.92)P-121 m/z = 884.29(C₆₄H₄₀N₂OS = 885.10) P-122 m/z = 996.23(C₆₈H₄₀N₂OS₃ =997.26) P-123 m/z = 1030.27(C₇₂H₄₂N₂O₂S₂ = 1031.26) P-124 m/z =886.30(C₈₄H₄₂N₂OS = 887.11) P-125 m/z = 1032.28(C₇₂H₄₄N₂O₂S₂ = 1033.28)P-126 m/z = 1050.33(C₇₆H₄₆N₂O₂S = 1051.28) P-127 m/z =1170.37(C₈₄H₅₄N₂OS₂ = 1171.49) P-128 m/z = 1206.40(C₈₈H₅₈N₂S₂ = 1207.57)P-129 m/z = 668.25(C₄₈H₃₂N₂O₂ = 668.80) P-130 m/z = 760.25(C₅₄H₃₆N₂OS =760.96) P-131 m/z = 684.22(C₄₈H₃₂N₂OS = 684.86) P-132 m/z =760.25(C₅₄H₃₆N₂OS = 760.96) P-133 m/z = 684.22(C₄₈H₃₂N₂OS = 684.86)P-134 m/z = 760.25(C₅₄H₃₈N₂OS = 760.96) P-135 m/z = 700.20(C₄₈H₃₂N₂S₂ =700.92) P-136 m/z = 912.32(C₆₆H₄₄N₂OS = 913.15) P-137 m/z =744.28(C₅₄H₃₆N₂O₂ = 744.89) P-138 m/z = 776.23(C₅₄H₃₆N₂S₂ = 777.02)P-139 m/z = 760.25(C₅₄H₃₆N₂OS = 760.96) P-140 m/z = 684.22(C₄₈H₃₂N₂OS =864.86) P-141 m/z = 740.29(C₅₂H₄₀N₂OS = 740.97) P-142 m/z =852.26(C₈₀H₄₀N₂S₂ = 853.11) P-143 m/z = 760.25(C₅₄H₃₆N₂OS = 760.96)P-144 m/z = 760.25(C₅₄H₃₆N₂OS = 760.96) P-145 m/z = 684.22(C₄₈H₃₂N₂OS =684.86) P-146 m/z = 820.31(C₆₀H₄₀N₂O₂ = 820.99) P-147 m/z =760.25(C₅₄H₃₆N₂OS = 760.96) P-148 m/z = 760.25(C₅₄H₃₆N₂OS = 760.96)P-149 m/z = 720.20(C₄₈H₃₀F₂N₂OS = 720.84) P-150 m/z = 700.20(C₄₈H₃₂N₂S₂= 700.92) P-151 m/z = 754.34(C₅₄H₂₆D₁₀N₂O₂ = 754.96)

Manufacturing Evaluation of Organic Electronic Element [Example 1] RedOrganic Light Emitting Device (Emitting-Auxiliary Layer)

An organic electroluminescent device was manufactured according to aconventional method using the compound of the present invention as anemitting-auxiliary layer material. First, after vacuum deposition of4,4′,4″-Tris[2-naphthyl(phenyl)amino]triphenylamine (abbreviated as2-TNATA) to a thickness of 60 nm on the ITO layer (anode) formed on aglass substrate to form a hole injection layer, on the hole injectionlayer,N,N′-bis(1-naphthalenyl)-N,N′-bis-phenyl-(1,1′-biphenyl)-4,4′-diamine(abbreviated as NPB) as a hole transport compound was vacuum-depositedto a thickness of 60 nm to form a hole transport layer. Then, aftervacuum deposition of the compound P-1 of the present invention to athickness of 40 nm on the hole transport layer to form an emittingauxiliary layer, by using 4,4′-N,N′-dicarbazole-biphenyl (abbreviated asCBP) as a host material andbis-(1-phenylisoquinolyl)iridium(III)acetylacetonate (hereinafter(piq)2lr(acac)) as a dopant material on the emitting-auxiliary layer,doping at a 95:5 weight ratio was vacuum-deposited on the emittingauxiliary layer to a thickness of 30 nm to form an emitting layer. Next,vacuum deposition of(1,1′-biphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum(hereinafter BAlq) to a thickness of 5 nm on the emitting layer to forma hole blocking layer, and bis(10-hydroxybenzo[h]quinolinato)beryllium(hereinafter BeBq₂) was vacuum-deposited to a thickness of 35 nm on thehole blocking layer to form an electron transport layer. Then, as anelectron injection layer, LiF, an alkali metal halide was deposited to athickness of 0.2 nm on the electron transport layer, then, on theelectron injection layer, Al was deposited to a thickness of 150 nm andused as a cathode to prepare an organic electroluminescent device.

[Example 2] to [Example 23]

An organic electroluminescent device was manufactured in the same manneras in Example 1, except that the compound of the present inventiondescribed in Table 4 was used instead of the compound P-1 of the presentinvention as an emitting-auxiliary layer material.

Comparative Example 1

An organic electroluminescent device was manufactured in the same manneras in Example 1, except that the emitting auxiliary layer was notformed.

[Comparative Example 2] to Comparative Example 6]

An organic electroluminescent device was manufactured in the same manneras in Example 1, except that the comparative compounds A to E were usedinstead of the compound P-1 of the present invention as an emittingauxiliary layer material.

By applying a forward bias DC voltage to the organic electroluminescentdevices prepared in Examples and Comparative Examples prepared in thisway, Electroluminescence (EL) characteristics were measured with PR-650from photo research, and as a result of the measurement, the T95lifetime was measured using a lifetime measuring device manufactured byMcScience at 2500 cd/m² standard luminance. Table 4 below shows thedevice fabrication and evaluation results.

TABLE 4 Current Density Brightness Efficiency compound Voltage (mA/cm²)(cd/m²) (cd/A) T(95) comparative — 6.7 32.5 2500 7.7 62.7 example (1)comparative comparative 5.9 13.6 2500 20.4 113.3 example (2) compound Acomparative comparative 5.7 10.3 2500 24.2 123.2 example (3) compound Bcomparative comparative 6.1 16.4 2500 15.2 121.0 example (4) compound Ccomparative comparative 5.9 10.8 2500 23.2 107.5 example (5) compound Dcomparative comparative 6.2 24.8 2500 10.1 82.3 example (6) compound Eexample (1) compound (P-1) 5.2 8.7 2500 28.9 147.9 example (2) compound(P-2) 5.4 8.9 2500 28.0 130.1 example (3) compound (P-49) 5.3 8.0 250031.2 146.1 example (4) compound (P-55) 5.0 7.6 2500 33.1 150.7 example(5) compound (P-83) 5.4 8.6 2500 29.1 133.7 example (6) compound (P-97)5.2 8.5 2500 29.4 139.3 example (7) compound (P-105) 5.0 8.1 2500 30.8143.6 example (8) compound (P-114) 5.2 8.5 2500 29.5 130.4 example (9)compound (P-118) 5.1 8.5 2500 29.3 143.8 example (10) compound (P-129)5.2 8.6 2500 29.2 145.3 example (11) compound (P-130) 5.2 8.8 2500 28.3137.0 example (12) compound (P-131) 5.3 7.9 2500 31.8 138.4 example (13)compound (P-133) 5.1 8.2 2500 30.6 150.6 example (14) compound (P-134)5.0 8.1 2500 30.9 152.2 example (15) compound (P-137) 5.1 8.4 2500 29.7152.3 example (16) compound (P-139) 5.1 8.6 2500 29.2 143.9 example (17)compound (P-143) 5.2 8.0 2500 31.1 141.2 example (18) compound (P-145)5.2 8.7 2500 28.7 134.4 example (19) compound (P-146) 5.3 8.7 2500 28.8133.1 example (20) compound (P-148) 5.1 7.9 2500 31.5 146.4 example (21)compound (P-149) 5.4 7.6 2500 32.7 131.8 example (22) compound (P-150)5.0 8.0 2500 31.3 146.2 example (23) compound (P-152) 5.0 8.1 2500 33.2150.8

Referring to Table 4, when a red organic light emitting device ismanufactured using the material for an organic electroluminescent deviceof the present invention as an emitting-auxiliary layer material, thedriving voltage, luminous efficiency and lifespan of the organicelectroluminescent device were remarkably improved compared toComparative Examples in which no emitting auxiliary layer was formed orin which Comparative Compounds A to E were used.

In other words, in Comparative Examples 2 to 6 using ComparativeCompounds A to E as an emitting auxiliary layer rather than ComparativeExample 1 in which the emitting auxiliary layer was not formed, thedriving voltage, efficiency, and lifespan of the device were improved,when the compound of the present invention was used as a material forthe emitting auxiliary layer, compared to when Comparative Compounds Ato E were used as the emitting auxiliary layer, the driving voltage ofthe organic electroluminescent device was lowered, and the luminousefficiency and lifespan were improved.

Comparing the comparative compound A or E and the compound of thepresent invention, it is the same as the structure in which dibenzofuranor dibenzothiophene is bonded between the amine and the amine, but thecompound of the present invention has a structure in which dibenzofuranor dibenzothiophene is further substituted with an amine group.Therefore, when dibenzofuran or dibenzothiophene is bonded to an aminegroup, the refractive index is significantly higher than when a generalaryl group substituent is substituted, and Tg also increases, so thatefficiency and thermal stability are excellent.

Also, the compound of the present invention is the same as inComparative Compound B in that an amine group is substituted fordibenzofuran or dibenzothiophene, but is different in that a linkinggroup between dibenzofuran or dibenzothiophene and an amine group isnecessarily present.

Accordingly, the compound of the present invention is different from thecomparative compound by introducing a linking group between thedibenzofuran or dibenzothiophene and the amine group, so that theconjugation length becomes longer than that of the comparative compoundB, as a result, the hole characteristics are improved, and as a result,the driving and efficiency are significantly increased compared to thecomparative compound, and the chemical stability for the unsharedelectron pair is increased, and the lifespan is also increased.

Comparing the comparative compound C and the compound of the presentinvention, the structure is the same as that of the present invention,but the bonding position of dibenzothiophene between the amine and theamine is the 3rd and 7th positions, and the position of thedibenzothiophene bonded to the amine is substituted with the 3rdposition. Table 5 below shows the HOMO electron clouds of thecomparative compound C and the compound P-55 of the present invention.

Referring to the Table 5, in the case of Comparative Compound C, theelectron cloud is widely spread over the two amine moieties, but it canbe seen that the compound of the present invention forms an electroncloud in a narrower region than that of the comparative compound, andthrough this, the hole mobility is improved and it is determined thatthe device characteristics are affected.

In addition, in order to confirm that the hole mobility is improved, anorganic electronic device was fabricated with ITO layer (anode)/2-TNATA60 nm/NPB 60 nm/Comparative compound C or compound P-55 of the presentinvention/HATCN 10 nm/Al (cathode) 150 nm and HOD (Hole Only Device) wasmeasured, and the results can be confirmed through FIG. 5 and Table 6below.

TABLE 6 Δ Op.V Op.V Δ Op.V Op.V Device @ 0.1 mA/cm2 @ 0.1 mA/cm2 @ 10mA/cm2 @ 10 mA/cm2 P-55 0.00 0.61 0.00 1.35 Ref. C 1.58 2.19 1.62 2.97

Referring to FIG. 5 and Table 6, it can be seen that at a currentdensity of 0.1 mA/cm², the driving voltage is 2.19 V for ComparativeCompound C and 0.61 V for Compound P-55 of the present invention, andthe difference between the comparative compound C and the compound P-55of the present invention is 1.58 V. Also, at a current density of 10mA/cm², the driving voltage is 2.97 V for Comparative Compound C and1.35 V for Compound P-55 of the present invention, and It can be seenthat the difference between Comparative Compound C and Compound P-55 ofthe present invention is 1.62 V. Through this, it can be seen that thecompound of the present invention has more improved hole mobilitycompared to Comparative Compound C.

That is, it is judged that the compound of the present inventionexhibits superior device characteristics compared to the comparativecompound C based on the above-mentioned points.

Comparing the comparative compound D and the compound of the presentinvention, Comparative Compound D has a structure in which a fluorenylgroup is introduced between an amine and an amine, and the compound ofthe present invention has a structure in which dibenzofuran ordibenzothiophene is bonded between the amine and the amine. It can beconfirmed that when dibenzofuran or dibenzothiophene is introduced, therefractive index is significantly higher than when a fluorenyl group isintroduced, and Tg is also increased, so that efficiency and thermalstability are improved.

In conclusion, although Comparative Compounds A to E and the compoundsof the present invention consist of similar components, a linking groupis introduced between dibenzofuran or dibenzothiophene and an aminegroup, so that the properties of the compound, such as holecharacteristics, light efficiency characteristics, hole injection &mobility characteristics, charge balance of holes and electrons, aremore suitable for the red emitting auxiliary layer, thereby the deviceresults of Examples 1 to 23 are significantly superior to those ofComparative Examples 2 to 6.

In the case of the emitting-auxiliary layer, since it is necessary tounderstand the correlation between the hole transport layer and theemitting layer (host), even if a similar core is used, it will be verydifficult to infer the characteristics of the emitting-auxiliary layerusing the compound of the present invention even for those of ordinaryskill in the art.

Also, in the evaluation results of the above-described devicefabrication, the device characteristics in which the compound of thepresent invention is applied only to the emitting-auxiliary layer hasbeen described, but the compound of the present invention may be appliedto the hole transport layer or both the hole transport layer and theemitting auxiliary layer may be applied.

Although exemplary embodiments of the present invention have beendescribed for illustrative purposes, those skilled in the art willappreciate that various modifications, additions and substitutions arepossible, without departing from the scope and spirit of the inventionas disclosed in the accompanying claims. Therefore, the embodimentdisclosed in the present invention is intended to illustrate the scopeof the technical idea of the present invention, and the scope of thepresent invention is not limited by the embodiment. The scope of thepresent invention shall be construed on the basis of the accompanyingclaims, and it shall be construed that all of the technical ideasincluded within the scope equivalent to the claims belong to the presentinvention.

What is claimed is:
 1. A compound represented by Formula 1:

wherein: 1) R¹, R², R³ and R⁴ are the same or different from each other,and are each independently selected from the group consisting ofhydrogen; deuterium; halogen; a C₆-C₆₀ aryl group; fluorenyl group; aC₂-C₆₀ heterocyclic group including at least one heteroatom of O, N, S,Si or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀aromatic ring; C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀alkynyl group; a C₁-C₃₀ alkoxy group; a C₆-C₃₀ aryloxy group; and anadjacent plurality of R¹s, or a plurality of R²s, or a plurality of R³s,or a plurality of R⁴s may be bonded to each other to form a ring, 2) Xand Y are independently of each other O or S, 3) L¹, L² and L³ are eachindependently selected from the group consisting of single bond; aC₆-C₆₀ arylene group; a fluorenylene group; a C₂-C₆₀ heterocyclic groupincluding at least one heteroatom of O, N, S, Si or P; and a fused ringgroup of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring, 4) L⁴ isselected from the group consisting of a C₆-C₆₀ arylene group; afluorenylene group; a C₂-C₆₀ heterocyclic group including at least oneheteroatom of O, N, S, Si or P; and a fused ring group of a C₃-C₆₀aliphatic ring and a C₆-C₆₀ aromatic ring, 5) Ar¹, Ar², Ar³, Ar⁴ and Ar⁵are each independently selected from the group consisting of a C₆-C₆₀aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclic group including atleast one heteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀aliphatic ring and a C₆-C₆₀ aromatic ring; a C₁-C₆₀ alkyl group; anC₂˜C₃₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxy group; aC₆-C₃₀ aryloxy group, 6) a and d are each independently an integer of 0to 4, b and c are each independently an integer of 0 to 3, m and n areeach independently 0 or 1, provided that m+n≥1, 7) d′ is an integer from0 to 3, 8) wherein the aryl group, arylene group, heterocyclic group,fluorenyl group, fluorenylene group, aliphatic ring group, fused ringgroup, alkyl group, alkenyl group, alkoxyl group and aryloxy group maybe substituted with one or more substituents selected from the groupconsisting of deuterium; halogen; silane group; siloxane group; borongroup; germanium group; cyano group; nitro group; C₁-C₂₀ alkylthiogroup; C₁-C₂₀ alkoxy group; C₁-C₂₀ alkyl group; C₂-C₂₀ alkenyl group;C₂-C₂₀ alkynyl group; C₆-C₂₀ aryl group; C₆-C₂₀ aryl group substitutedwith deuterium; a fluorenyl group; C₂˜C₂₀ heterocyclic group; C₃-C₂₀cycloalkyl group; C₇-C₂₀ arylalkyl group; C₈-C₂₀ arylalkenyl group; andthe substituents may be bonded to each other to form a saturated orunsaturated ring, wherein the term ‘ring’ means a C₃-C₆₀ aliphatic ringor a C₆-C₆₀ aromatic ring or a C₂-C₆₀ heterocyclic group or a fused ringformed by the combination thereof, and 9) wherein a compound of Formula7 is excluded from the compound of Formula 1:


2. The compound of claim 1, wherein L¹, L², L³ and L⁴ are represented byany one of Formulas b-1 to b-13:

wherein: 1) Z is O, S, C(R¹³)(R¹⁴) or N-L⁵-Ar⁶, 2) Z¹, Z², Z³, Z⁴ and Z⁵are each independently N or C(R¹⁵), provided that at least one of Z¹,Z², Z³, Z⁴ and Z⁵ is C(R¹⁵) and at least one thereof is N, 3) R⁵, R⁶,R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴ and R¹⁵ are the same as thedefinition of R¹ in Formula 1 of claim 1, or adjacent groups may combinewith each other to form a ring, 4) e, g, h and l are each independentlyan integer of 0 to 4, f is an integer of 0 to 6, i and j are eachindependently an integer of 0 to 3, k is an integer of 0 to 2, 5) Ar⁶ isthe same as the definition of Ar¹ in Formula 1 of claim 1, 6) L⁵ is thesame as the definition of L¹ in Formula 1 of claim 1, 7)

indicates the binding position.
 3. The compound of claim 1, wherein thecompound of Formula 1 is represented by one of Formulas 1-1 to 1-3:

wherein: 1) R¹, R², R³, R⁴, X, Y, L¹, L², L³, L⁴, Ar¹, Ar², Ar³, Ar⁴,Ar⁵, a, b, c and d are the same as defined in claim 1, 2) c′ is aninteger from 0 to 2, and d′ is an integer from 0 to
 3. 4. The compoundof claim 1, wherein the compound of Formula 1 is represented by one ofFormulas 2-1 to 2-4:

wherein: R¹, R², R³, R⁴, X, Y, L¹, L², L³, L⁴, Ar¹, Ar², Ar³, Ar⁴, Ar⁵,a, b, c, d, m and n are the same as defined in claim
 1. 5. The compoundof claim 1, wherein the compound of Formula 1 is represented by one ofFormulas 3-1 to 3-14:

wherein: 1) R¹, R², R³, R⁴, X, Y, L¹, L², L³, L⁴, Ar¹, Ar², Ar³, Ar⁴,Ar⁵, a, b, c and d are the same as defined in claim 1, 2) c′ is aninteger from 0 to 2, and d′ is an integer from 0 to
 3. 6. The compoundof claim 1, wherein the compound of Formula 1 is represented by one ofFormulas 4-1 to 4-6:

wherein: 1) R¹, R², R³, R⁴, X, Y, L¹, L², L³, Ar¹, Ar², Ar³, Ar⁴, Ar⁵,a, b, c, d, m and n are the same as defined in claim 1, 2) R⁵, R⁶, R⁷,R⁹, R¹⁰, R¹¹, R¹², e, f, g, i, j, k, l and Z are the same as defined inclaim
 2. 7. The compound of claim 1, wherein the compound of Formula 1is represented by one of Formulas 5-1 to 5-4:

wherein R¹, R², R³, R⁴, X, Y, L¹, L², L³, L⁴, Ar¹, Ar², Ar³, Ar⁴, Ar⁵,a, b, c, d, m and n are the same as defined in claim
 1. 8. The compoundof claim 1, wherein the compound represented by Formula 1 is selectedfrom the group consisting of compounds P-1 to P-152:


9. An organic electronic element comprising an anode, a cathode, and anorganic material layer formed between the anode and the cathode, whereinthe organic material layer comprises a single compound or 2 or morecompounds represented by Formula 1 of claim
 1. 10. The organicelectronic element of claim 9, wherein the organic material layercomprises at least one of a hole injection layer, a hole transportlayer, an emitting layer, an emitting-auxiliary layer, an electrontransport auxiliary layer, an electron transport layer, and an electroninjection layer.
 11. The organic electronic element of claim 9, whereinthe organic material layer is an emitting-auxiliary layer.
 12. Theorganic electronic element of claim 9, wherein the organic materiallayer is a hole transport layer.
 13. The organic electronic element ofclaim 9, further comprising a light efficiency enhancing layer formed onat least one surface opposite to the organic material layer among onesurface of the anode and the cathode.
 14. The organic electronic elementof claim 9, wherein the organic material layer is a light efficiencyenhancing layer.
 15. The organic electronic element of claim 9, whereinthe organic material layer comprises 2 or more stacks including a holetransport layer, an emitting layer, and an electron transport layersequentially formed on the anode.
 16. The organic electronic element ofclaim 9, wherein the organic material layer further comprises a chargegenerating layer formed between the 2 or more stacks.
 17. An electronicdevice comprising: a display device including the organic electronicelement of claim 9; and a control unit for driving the display device.18. The organic electronic element of claim 17, wherein the organicelectronic element is any one of an organic electroluminescent device(OLED), an organic solar cell, an organic photoreceptor (OPC), anorganic transistor (organic TFT), and an element for monochromic orwhite illumination.